


Behind the door

by Cagedandfree



Category: Supernatural
Genre: Age Play Little Castiel (Supernatural), Alternate Universe - College/University, Anal Fingering, Blow Jobs, Bottom Castiel, Butt Plugs, Caring Sam Winchester, Crossdressing, Crossdressing Castiel, Daddy Kink, Daddy Sam, Diapers, Dom/sub Undertones, Emotional Hurt/Comfort, Feminization, Finger Sucking, Fluff, Gags, Hand Jobs, Infantilism, Light Dom/sub, M/M, Massage, Medical Examination, Medical Kink, Non-Sexual Age Play, Orgasm Delay/Denial, Panty Kink, Rectal Temperature Taking, Roleplay, Sam Winchester Takes Care of Castiel, Sick Castiel, Spanking, Teasing, Top Sam Winchester, latex glove kink
Language: English
Status: Completed
Published: 2018-01-31
Updated: 2018-04-19
Packaged: 2019-03-11 19:06:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 28
Words: 21,236
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13530678
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: Castiel is nervous about meeting his college roommate and worried about what they will think. Luckily it is sam Winchester and he is open.





	1. Meeting the roommate

Castiel was nervous. Last year he had his own room in residence, but this year he wasn’t so lucky. He had to share a room with some stranger and it was going to be hard. 

Castiel walked to his dorm room and saw that the door was open and his roommate was already there. He sighed and walked in, closing the door.

“Hi. I’m Sam Winchester” the boy said. He stood up to shake Castiel’s hand and fuck not only was he tall, but he was hot as hell. 

“Uh-Hi. Castiel Novak.” He said.

“This your first year?”

“No. Second. You?” Castiel put his stuff on his bed.

“My first year. I took a year off though. I’m nineteen.” Sam said. He seemed nice.

“I did that too. I’m twenty.” Castiel replied.

“Are you okay?” Castiel noticed the concern in his voice and thought it was sweet.

“Uh-just nervous. I had a private room last year.”

“Wow. What was that like?”

“Nice” he said with a small smile and Sam laughed. God, he had a beautiful smile. He was probably straight though.

“What are you studying?” Sam asked.

“Religion. You?”

“Law.”

“Oh wow.”

Sam noticed that Castiel hadn’t started to unpack yet.

“Are you going to unpack?”

“Uh, maybe later.” 

“Well, it’s nice that we get our own bathroom. We don’t have to share with anyone else.” Sam smiled getting his desk ready. He heard Castiel sigh in relief. “Unfortunately , we don’t have a shower curtain.”

“O-Oh” Castiel looked down. He jumped a little when he felt Sam’s finger under his chin. His head was lifted up.

“Castiel. Is there something I should know?” Sam asked in a low voice. Castiel swallowed.

“It’s humiliating.” Castiel said. 

“We’re going to be spending a lot of time together.” Sam said looking into Castiel’s eyes.

“Do you like boys?” Castiel blurted out and Sam chuckled. He let go of Castiel’s chin.

“I do. Is that going to be a problem?” Sam stood taller if that was possible and Castiel shook his head.

“I-I do too” he stammered.

“I see.” Sam took a step back. “I’m a top. Are you a bottom?” Castiel nodded. “I’m not asking to have sex with you, unless you want it. I’m just letting you know.”

“I-I-I. I have a small penis.” Castiel said quickly and dropping his head. Sam raised an eyebrow. 

“How small?”

“Two inches” Castiel closed his eyes and Sam breathed out.

“Is there anything else you would like to tell me?” Sam’s voice was soft and gentle now. Castiel shook his head and felt Sam’s warm hand on his cheek. “May I kiss you?” Castiel looked up at his roommate with wide eyes.

“Re-really?” Sam nodded. “I would like that” Castiel said.

Sam kissed him gently at first and then the kiss got more passionate. He pulled away and brushed a thumb against Castiel’s lip. 

“I-I had a dom.” Castiel confessed. He had no idea what it was about his roommate that he literally just met, but something made Castiel want to share pretty much everything. “He hurt me. Not physically, but emotionally” 

“I’m sorry to hear that. I know we just met, but I am here to listen if you ever want to talk.” Sam said holding Castiel’s hands . 

“I do want to talk about it Sam, I want to share, but I don’t want to scare you. I don’t want you to think I’m a freak.” 

“I wont think you’re a freak. I promise. You have shared with me, I will share something with you.” Sam offered.

“Oh, only if you want to. Castiel said.

“I do want to.” Sam smiled. “I was a dom. My high school boyfriend Gabriel. We mutually decided to part ways before going off to school.” 

“That must have been hard.” Castiel said.

“That’s why we took the year off. We both knew that we were going to part ways. So we dedicated a year to each other. I passed him off to my older brother Dean.”

“And what about you?”

“Well. I was hoping to find a new sub here. Even my roommate.” Sam smirked a bit. Castiel blushed. “It was just a thought though. We don’t have to. I would be surprised.” 

“I do want that. However, I need some time to think about it.” Castiel said. Sam nodded.

That night the boys were back in their room. Castiel had unpacked his things without Sam seeing. He didn’t want to let his roommate see what he had hidden. Sam was reading when Castiel spoke again.

“I told my dom that-“ Castiel stopped talking.

“That what?” Sam asked sweetly, putting his book down.

“I-uh-I like feminization. I like dressing up really pretty, wearing make-up, heels, headbands.” The blue eye man confessed.

“Panties?” Sam asked sitting up. Castiel noticed that his eyes lit up a bit.

“Yes.”

“Castiel. I would like to see your penis. If you’re okay with that.” Sam said.

“Par-pardon.” Castiel stammered. Sam sat up, swinging his legs over the bed and sitting up. 

“You don’t have to.” Sam said

Castiel stood up and walked over, standing between Sam’s legs. Sam placed his hands on Castiel’s waist band of his pajama pants and looked up at him. Castiel nodded. Sam pulled the pants down and starred at Castiel’s small cock.

“Feminization?” Sam said looking up.

“Mm Hmm” Castiel whimpered.

“You’re small little cock, looks like a nice pretty clit.” Sam said rubbing his thumb over it. Castiel gasped and nodded. “And your ass. More like a pretty pussy, wouldn’t you say, baby girl?” Sam asked standing up and cupping Castiel’s cheek.

“Yes.” Castiel breathed.

“Do you want to be my pretty girl? In here, in this room. No one has to know.”

“Yes, Sam. Yes…sir.” Sam smiled at that.

“Sir. I like it. Castiel. I will take care of you. You want to be a pretty girl for me?”

“Yes.”

“Okay, sweetheart. In here, you will be.” Castiel smiled. Sam sat back down on his bed and pulled Castiel’s pants back up.


	2. Talking it thorugh and starting it slow

Castiel woke up and Sam was there with coffee for both of them. Both boys had the day off and they agreed to stay in.

“Morning, sweetheart” Sam smiled, handing the older boy’s coffee.

“Good morning, Sam” Castiel smiled taking the coffee.

“Are you ready for today?”

“I am. I’m nervous too.” Sam stroked Castiel’s hair and kissed his forehead. 

“So am I.” he smiled a bit.

“Sam, may I ask a question?” 

“Of course, Castiel.” Sam went and sat on his bed.

“May I ask about what you did with Gabriel. What kind of a dom you were?” 

“Sometimes I was harsh. Most of the time, I was caring.” 

“Harsh?”

“Watersports, name calling, slapping. One night, he wanted to be my dirty whore. He was kneeling, I spat in his face, came all over him, pissed all over him.”

“Oh…my….god.” Sam notices the slight panicked look on Castiel’s face.

“Oh. No! No, Castiel, that’s just what we both liked.”

“But, I’m not like that.”

Sam put his coffee down and went to kneel in front on Castiel he wrapped his arms around Castiel’s waist and looked up at him.

“I am a lucky dom who got to try my weirdest kinks with a wonderful sub. However, now I’ve found you, who likes something else. It’ll be nice to do something different. Show a softer side. Not that I wasn’t gentle with Gabriel, I was. Trust me Castiel. It’s about what we both need.” Castiel smiled and nodded.

“Thank you, Sam.” Castiel blushed. Sam stood up and kissed Castiel again. “I think I would like to get dressed. Take a shower, shave.” Castiel spoke slowly.

“Okay.” Sam smiled.

Castiel got up, grabbed a pack her packed to get changed and walked to the bathroom. Castiel took a deep breath. He turned the shower on and got undressed. He got in and felt the hot water on him. He took another deep breath.

It’s not official yet, but Sam seemed like he would be an amazing dom. Castiel shaved his under arms, Then his legs and carefully around his penis. Castiel was always embarrassed about his small cock. He hated to shower in gym class. His dom said it didn’t bother him, but Castiel knew better. Once he was clean and dry, he stepped out. He put cream on, making sure he would be all smooth.

Castiel slipped hot pink lace panties on. He pulled on a short black skirt and black heels. Castiel slipped on a white crop tank top and a black headband in his hair. He put on black eyeliner, mascara . He wasn’t much for eye shadow. He put on bright red lipstick and gloss on top. 

He looked at himself and then took a deep breath and opened the door. Sam looked up and smiled, seeing Castiel. 

“Do you like it, sir?”Castiel whispered.

“Yeah, baby girl, I think you look beautiful.” Sam said “come here” 

Castiel walked over and stood between Sam’s spread legs. Sam rubbed a hand up and down Castiel’s smooth legs. He looked up at Castiel and cupped his ass, giving it a firm squeeze.

“Lace panties?” Sam smiled.

“Hot pink, sir.” Castiel blushed.

“Would it be alright if I gave you a little spank?” Castiel nodded and Sam gave a light smack to his ass and removed his hand.

“Is there anything I can do for you?” Castiel whispered

“You can turn around and bend over. I want to see your hot pink panties.” 

Castiel smiled a bit and turn around. He knew and so did Sam that his skirt was so short that bending over he could easily see. He bent over and heard Sam groan. Sam stood up and placed his large hands on Castiel’s waist and had him stand up. He reached a hand forward and rubbed Castiel’s cock over his panties.

“What’s this called?” Sam whispered low in his ear.

“My clit, sir.” Castiel breathed out. Sam sucked on Castiel’s earlobe and brought his hand to Castiel’s ass and tapped his hole.

“And this?”

“M-my pussy.” 

Sam wrapped his arms around Castiel’s waist and kissed down his neck, sucking at his pulse point. Castiel tilted his head back.

“What a good girl you’re being for me.” Sam murmured against his neck.

Sam turned Castiel around and cupped his cheek kissing him gently. Sam walked Castiel backwards against Castiel’s bed and laid him down. Sam hovered over him and kissed down his neck and reached a hand down reaching a hand into the panties and rubbed Castiel. Castiel gasped.

“Mmm, does that feel good, baby girl?” 

“Yes, sir. That feels so good.”

“You’re a beautiful girl, Castiel.”

“Suck my clit. Please!” Castiel begged.

“Oh sweetheart, we’ll get there.” Sam smirked removing his hand from the panties. “But right now, I want you to dance.”

“Wh-what?” 

“Show me how badly you want me to suck your little clit. Put on show for me. Dance like the good girl you are.”

Sam stood up and walked over to the chair and sat down. Castiel stood up and walked to stand in front of Sam. 

Castiel swayed side to side. He bent down and opened his legs flashing Sam his underpants. Sam was impressed that Castiel could dance so well in the heels. Castiel stood up and danced turning around. be bent down and stood up ass sticking out. He moved his hips side to side. He turned to face Sam and paused. Sam had his cock out and was stroking it. Castiel took a chance.

“You like this sir? You like me showing you what a good girl I want to be. You like me showing you how badly I want you to rub my clit?” Sam groaned giving his cock a tug.

“Be a good girl and get on your knees, finish me off. You will keep my cum in your mouth for five minutes before you swallow” this time Castiel groaned and walked over sinking to his knees.

“Yes sir, whatever pleases you.”


	3. You're safe, you're loved

Sam grunted and came in Castiel’s mouth. He pulled off with a pop and shut his mouth sitting back on his heels. Sam stroked Castiel’s cheek.

“Good girl” Sam said cupping Casitel’s chin. “Now you keep that in your mouth for five minutes and then I’m going to suck your clit. Make you feel real good” Sam said his face inches from Castiel’s. “Now, you don’t swallow until I give you permission.” Castiel smiled.

Castiel sat with his hands folded in his lap, his back straight. Sam set an alarm and went to clean himself up. He came back out grabbed his law book and came back, setting them up. Finally the alarm went off. Sam turned it off. 

“Baby girl, I want you to swallow that.” Sam said reaching into his desk drawer and pulling out a latex glove, snapping it on. Castiel did. “Good girl. Now, open your mouth let me inspect it.”

Castiel felt a shudder down his spine. He opened his mouth. His ungloved hand gripped his chin and his two gloved fingers felt around his mouth. Sam pulled his fingers out and Castiel closed his mouth. Sam brushed his gloved thumb against Castiel’s lips and pulled the lower one down.

“Did you like the taste of that?” Castiel nodded. Sam pushed his thumb past Castiel’s lips. “Going to show me how you want me to suck your clit?”

“Mmm” Castiel moaned around Sam’s thumb. Sam’s none gloved hand rubbed the back of Castiel’s neck. Castiel swirled his tongue around Sam’s thumb. 

“Uh huh. Like that. Good girl.” Sam pulled his thumb out, smudging Castiel’s lipstick a bit. Sam took the glove off and threw it away.

“Sir?” Castiel spoke, not moving from his passion.

“Yeah, baby girl?”

“Why the glove?” Sam smirked a bit.

“I have a bit of a latex glove kink. When I have you hold and swallow, I will inspect your mouth.”

“It was hot, sir.” Castiel blushed.

“Glad to hear.” Sam stroked Castiel’s cheek. “You can stand up, sweetheart” Sam smiled, not giving him permission, just letting him know. Sam held out a hand and Castiel took it, standing up. He smoothed down his dress. “Now, I’m not going to suck your clit today, baby girl. I don’t want to rush into things.”

“Yes, sir. Thank you.” 

“Smudged your lipstick a bit, do you want to fix it?”

“No. I want to keep it like this as a reminder that I was a good girl.” Castiel batted his eye lashes. 

It was 11:30 now; both boys were getting ready for their classes. However Castiel kept his legs spread so Sam could look at his hot pink panties. 

“Baby girl, do you want me to get lunch or do you want to go out with me?”

“I would like to leave the room, sir.”

“Okay.” Sam smiled.

“Can I wear my pretty pink panties under my sweats?” Castiel asked, putting his book down and spreading his legs more.

“Yes. Now, can you do me a favor. Can you go get changed now.” 

Castiel nodded and grabbed his sweatpants and t-shirt. He slipped his heels off, unzipped his skirt and let it fall. He folded it nicely. He took his crop top off and folded that too. He slipped his sweatpants on and t-shirt. He walked to the bathroom and wiped off his make-up. When he came back, he saw Sam sitting in his chair, facing the door. 

“Good job. Please come straddle my lap, facing me” Sam said calmly.

Castiel did, wrapping his arms around Sam’s neck. Sam wrapped one around Castiel’s waist and with his other, gently guided Castiel’s head to his shoulder. Sam held him tight and rubbed a hand on his back. 

“There we go. You just relax and let me hold you. I will do this with you every time you get out of your pretty clothes.” Sam whispered kissing the side of his head.

Castiel’s old dom never really was one for aftercare. He usually had Castiel clean himself up and that was it. However Sam has already proved himself to be an amazing dom. Sam just soothed him and Castiel broke into sobs. He was never taken care of like this. 

“I’ve got you, sweetheart. You’re safe. You’re loved.” Sam whispered. He knew that when Castiel was ready, he would open up. Finally the sobs subsided. 

“I-I’m sorry, Sam. Sir!” he corrected.

“When you’re not in a skirt, dress or just your panties, Sam is perfect.” Sam whispered. Castiel nodded. “Castiel, when you’re ready I would like to know what happened.” Sam whispered.

“M-my dom never-“ Castiel started and whimpered.

“When you’re ready.” Sam spoke again. “What’s going to happen is we’re going to stay here like this, I’m going to hold you. Then we’ll get lunch. After that, if you’re ready, I’m here to listen.”

“Thank you, Sam” Castiel whispered.

“Look at me” Castiel looked at Sam and he stroked his cheek. Sam gently kissed Castiel’s lips. “You are beautiful and loved. Do you understand?” Castiel nodded.

Sam guided Castiel’s head back to his shoulder and they stayed like that until lunch.

**Notes for the Chapter:**

> Anything you want to see.


	4. Being a good girl

**Notes for the Chapter:**

> Two in one day

Castiel and Sam walked to the cafeteria. Once Sam and Castiel got their food, they sat at a table and ate. Castiel took his shoe off and dragged it up Sam’s leg. Sam smirked; Castiel kept running his foot up and down Sam’s leg. When the meal was done, he put his shoe on and they walked back to the room.

“Castiel, are you ready to talk?” Sam asked.

“Yes, Sam.” he nodded. Sam sat on his bed and crossed his legs and Castiel sat on Sam’s bed facing him. “My old dom…he never was one for aftercare.” Castiel looked down and Sam gasped a bit.

“He never took care of you after?” Sam was horrified. 

“No. He had me clean myself up. He never held me after or told me I did a good job. I was just overwhelmed with your kindness. You told me I was loved and I-it’s really nice.”

“Castiel, I am so sorry that happened to you. Aftercare is so impotent, no matter how small the scene or whatever is. Is it alright, if I hold you for a bit?” 

“As a pretty girl?”

“I can if that is what you would like, but right now, I would like to hold you. Castiel.”

“I would like that."

Sam stretched out and Castiel moved so he was lying between Sam’s legs against his chest. Sam wrapped his arms around the older boy and held him close. How could someone take advantage of Castiel. He seemed like he would be a great sub. He already was and it hasn’t even been 24 hours yet. 

“Castiel, I would like to take care of you. I would like to be your dom. I won’t hurt you, I would never let anything hurt you. Dean and I eased Gabriel to switching doms. He called me this morning well I was getting coffee, said he is ready to be collared.”

“What does that mean?” Castiel whispered and Sam stroked his hair.

“It means that Gabriel is going to permanently be Dean’s. No other dom. I’m telling you this, because I don’t want you to think that I would switch back to Gabriel if I had the chance. They are a making it official. I am so proud of them. I want you to know that I am yours. If you’ll have me” 

“Would you collar me?” Castiel asked sitting up to look at Sam.

“If you we both wanted that, yes. But as I said. We’ll take it slow.” 

Castiel sat up and kissed Sam, straddling his lap. Sam slid a hand down the back of Castiel’s sweatpants and grabbed his ass. Castiel kissed down Sam’s neck.

“Let me get dress again. Can I be your pretty girl” Castiel whispered kissing Sam’s lips again.

“I want you to be comfortable baby girl. Why don’t you wear my t-shirt, those heels, make your face real pretty and those panties and that’s all.”

“Yes sir.” Castiel got off the bed.

He pulled the sweatpants off and his t-shirt, putting the shirt Sam just took off on. He picked up his clothes. Folded them, slipped the heels on and went to the bathroom to doll up his face. When he came out, Sam was there and he cupped Castiel’s balls and cock.

“Who does this belong to?” he whispered in Castiel’s ear.

“You, sir.” Castiel whispered.

“It sure does, pretty girl” Sam said stroking the back of his finger down Castiel’s cheek. He smacked Castiel’s ass. “And this?”

“All yours, sir. This is all yours.” 

Sam got on his knees and ran a hand up Castiel’s smooth legs. He lifted the shirt, that just barely covered Castiel’s ass and kissed his stomach. He placed a little peck on Castiel’s cock.

“Mmm” Castiel moaned.

“Yeah. You like that that?” Sam did it again “you like when I kiss your clit?”

“Mm hmm”

“Yeah? Getting you nice and hard, huh?” Sam did it again and Castiel was embarrassingly was erect. Sam circled his thumb over Castiel’s tip. “Yeah, pretty clit, for a pretty girl” Sam stood up and kissed Castiel’s lips.

“Sir, please.” Castiel whimpered. 

“No, baby doll, you’re not going to cum yet.” Sam murmured against his lips. “You’re going to be a good girl, right?” 

“Yes.” He breathed out.

“Do you have anything else you want to show me, baby girl? Anything at all? I told you about my latex glove kink.” Castiel swallowed and nodded. “Like I said before, I have done pretty much everything, except pain and knife play.” 

Castiel nodded again and walked to his bed and knelt down. He pulled out this box he had and stood up, placing it on Sam’s desk. He opened it and Sam saw a ball gag and a heart shaped pink butt plug. Sam walked over and ran the back of his hand down Castiel’s cheek.

“These are wonderful.” Sam smiled.

“Thank you, sir.”

“Would you like to be wearing these now?”

“Oh” Castiel blushed. He did. If he was going to submit to Sam, he wanted to wear these. “I would sir, I want to be your girl, but I would like to be wearing a dress as well.” Sam cupped Castiel’s cheek and kissed him.

“Baby girl, you go pick out whatever pretty dress you want and put it on.” he smiled and Castiel did too.

“Sir, should I change my panties too? Make them black, it’ll match the dress.” Sam smiled softly and nodded.

Castiel put away his folded clothes. Sam locked the door, though he knew no one was going to come in. Castiel took off his pink panties and folded them. He took off Sam’s shirt and folded that. He looked down at his still erect cock. He slid on the black lace panties and grabbed a black dress. 

It was backless, just covered his ass. He slid it on and walked back over to Sam. He was happy that the floors we carpeted and they couldn’t hear the clacking of the heels.

“Do you like it sir?” Castiel batted his eye lashes again.

“Very much. Give me a slow spin.” Castiel did. “Good.” Sam picked up the ball gag and walked over to Castiel. “Open up.” Castiel did and Sam placed the gag on him, doing it up. “on the bed, hands and knees.”

Castiel obeyed and he heard Sam slip on a latex glove and the popping of the lube cap. His ungloved hand pulled down Castiel’s panties. Castiel gave a little yelp when the lube hit is ass.

“Sorry, baby girl” Sam mock pouted rubbing a gloved finger over his ass. “Relax your pussy for me. Going to plug it up.”

Castiel easily relaxed. Sam was firm, but gentle. He tensed a little when Sam slid his finger in, but relaxed instantly. Sam worked Castiel open and worked another finger in him. He pulled out and Castiel whimpered.

“Deep breath.” Sam instructed and Castiel did, feeling the lubed plug against his hole. “And out” Castiel did and Sam slid the plug in with ease. “Very good. Good girl. You’re pussy is all full now,” Sam said snapping off the glove and pulling the panties back up. “Stand up” 

Castiel stood up and Sam circled him like prey. He rubbed a hand on his cheek. He tapped the plug in his ass. Castiel looked beautiful. Black dress, panties, heels. Bright red lipstick with a black ball gag between his lips. Eye shadow and mascara. Sam took Castiel’s hands and kissed his forehead.

“I have to read the first chapter of my book. Do you think you could be a good girl and get on your elbows and knees, face towards me, ass in the air?” Castiel nodded and assumed the position. Sam opened the book and ran a hand over Castiel’s ass and tapped the plug. “Good girl” Sam smiled and opened his book.


	5. Nurse Novak

**Notes for the Chapter:**

> Third chapter

Midterms were really getting to Sam. He was studying so much. Castiel walked around in panties and Sam’s t-shirt, but Sam still hadn’t sucked Castiel’s cock. It was mid-October, Castiel left to get something, a surprise he had for Sam. They planned to stay in that night. 

Sam was shirtless, wearing his pajama pants studying at the desk when Castiel walked in. He placed the bag that he bought in the bathroom and walked over to Sam. He placed his hands on his shoulders and started to massage.

“Mmm baby, that feels soo good.” Sam groaned, relaxing a bit.

“You’ve been working yourself.” Castiel said massing the base of Sam’s skull. 

“I know, but this is important.” 

“Mmm, give me a few more minutes, then I’m all yours.” Sam smiled.

“Okay.”

Castiel went to the bathroom to get ready. He was already wearing white lace panties. He took off his sweats and t-shirt and pulled out the nurses out. He pulled on the white knee high stockings and slipped on the dress that showed a bit of his ass. The pink plug nice in him. 

Sam has made it a rule now that if Castiel is to leave the room, he is to have the plug in. Reminding him who he belongs too. He stepped into the white high heels and got his make-up on. Making the eyeliner thicker. He put the gloss cover over the bright red lipstick and put the stethoscope around his neck. He opened the door.

“Sir?” Castiel spoke.

“I’m a minute.” Sam said.

Castiel walked over and placed his fingers on Sam’s neck feeling his pulse. He moved his hand to Sam’s forehead.

“Pulse is fast. Slight raise in temperature.” Castiel stepped to the side so Sam could see him. “Mr. Winchester, my name is nurse Novak and I think you need an examination.” Sam raised an eyebrow.

“Oh, you do?” he smirked

“Yes.” 

Castiel bent down to open the drawer where he knew Sam kept his gloves. When he stood up, his made sure Sam got a clear shot of his ass, with the plug. Sam let out a groan. Castiel turned around and slowly put the latex gloves on. He took the stethoscope off and breathed on it to warm it up. He stood between Sam’s legs and leaned forward, placing it on his chest. Castiel ran a gloved finger against Sam’s lips.

“Heart’s a bit fast. I guess, I need to conduct a deeper examination.” 

Castiel took the stethoscope off and straddled Sam’s lap. Castiel placed a kiss on Sam’s neck leaving a lipstick mark. Sam cupped Castiel’s ass. Castiel placed a kiss on Sam’s heart, leaving another mark. Castiel brushed his finger against Sam’s lips again and Sam parted them and started sucking on his gloved finger.

“Mmm. Good responses.” Castiel said feeling a tent grow in Sam’s pants. 

Castiel ground his hips down and Sam let out a groan. Castiel pulled his finger out and got off, getting on his knees. Castiel placed his hands on the waist band.

“Better take it this off to get a better look”

“Yes nurse Novak” Sam said and Castiel pulled his pants down, Sam lifting his hips to help. “That’s better.” 

Castiel wrapped his mouth around Sam’s cock. He cupped his balls and squeezed. Sam groaned and Castiel lifted his head up and started to stroke Sam’s cock, giving it a few tugs.

“You’re doing very well, Mr. Winchester. Is this removing any stress?”

“Yes.” Sam tilted his head back. 

Castiel wrapped his mouth around Sam’s cock again and Sam wrapped his hand around Castiel’s neck. Castiel licked the tip, of pre-cum. Castiel rubbed Sam’s inner thighs. Sam squeezed his eyes shut and came in Castiel’s mouth. Sam pulled out. 

“You can swallow.” Sam whispered, opening his eyes. Castiel did.

“Very good, Mr. Winchester. I’m going to clean you up.” 

Castiel left quickly, stripping the gloves and grabbed a warm wash cloth. He came back and cleaned Sam’s cock and put the cloth down and helped Sam back in his pants.

“Thank you so much, Nurse Novak.” 

“I’m going to give you a massage.” Sam smiled and nodded.

Castiel helped Sam on the bed, lying him down. Castiel grabbed the massage oils and straddled his back. Castiel loved the moans coming from Sam. He felt his dom relax. 

“You work so hard, I just wanted to do something nice.” Castiel whispered.

“It was perfect, baby girl. Thank you so much.”

“You can fall asleep.” Castiel said massaging Sam’s head.

“I’d love that baby, but I need to hold you after, okay?”

“Yes sir.”


	6. Sir getting his girl off

Castiel was doing homework. He had friends over, so he was in his sweatpants and a shirt. However the butt plug was still in. Now he was just alone withSam.

“Castiel, is there something you want to try?” Sam asked.

“Hm?” Castiel looked up from his homework.

“Well, you dressed as a very sexy nurse for me. Which I loved and I did think about asking you to do that.”

“You were?” Castiel put his book down.

“Yes. Is there something I can do?”

“There was something…I was thinking about…but”

“Go on.” Sam encouraged. 

“I had a corset and fishnets, thigh highs and booty shorts. I’m taken to the police station and stripped searched.”

“Are you a prostitute?” Sam asked.

“Lady of the night, Sam. And no, stripper, who got a little drunk in public and handsy with the arresting officer.” 

“I like that idea. Handcuffs okay?” Sam asked.

“Yes Sam.” Castiel smiled.

“Very good. We will do that Friday night.” 

“Name calling…only for that scene though.” Castiel said.

“Of course. Now, I know your friends were here, but we still have a few hours before bed. I’m going to shower.”

“Can I-uh-can I put on panties, get all pretty.” Castiel blushed. 

“Of course, Castiel. When we’re alone, if you want to do that, you go ahead. You don’t need my permission.” 

Sam went to take a shower and Castiel hot in his black panties and a crop, pink t-shirt that was sweatshirt material. Slipped on black high heels and a headband.

He set up a little mirror and did his makeup. When he was done he laid on his stomach and opened his book and kept reading. Sam walked over for the shower, drying his hair and wearing pajamas. 

“Sir, do you like?” Castiel asked.

“Yeah baby girl. Come here.” 

Castiel stood up and walked over. Sam took his hand and gave him a spin. 

“You look so damn sexy, pretty girl” Sam said grabbing Castiel’s ass and giving it a squeeze. He placed open mouth kisses on Castiel’s neck. He cupped his cheek and looked Castiel in the eyes. “How about you be a good girl and go on the bed and spread your legs for me.”

“Yes sir” Castiel shuddered. Was this it? Was Sam finally going to pleasure him. 

Castiel got on the bed and spread his legs. Sam crawled between them and kissed above his cock. Sam kissed up his stomach and circled his tongue on around his nipple, sucking on it.

“Mmm, Sir.”

“You like that?” Sam did it again, lightly biting it. 

Castiel carded his hand through Sam’s hair. Sam kissed lower and lower. He bit the waistband of his panties and pulled it off with his teeth. 

“Fuck, sir. Please! Suck my clit, please!”

Sam wrapped his mouth around Castiel’s cock. Castiel bucked his hips and Sam’s hands held him down. Castiel threw his head back, fisting the sheets and Sam’s hair.

“Finger my pussy.” He begged.

“Tsk. Tsk. Tsk. So greedy, sweetheart.” Sam kept sucking.

“PLEASE!” Castiel begged.

Sam sat back and looked at Castiel’s pleading. Sam stood up and grabbed a latex glove and slipped it on his left hand and climbed back on top of Castiel. His small cock nice and hard. Castiel parted his lips and Sam stuck his finger in. Castiel wrapped his mouth around the finger and started to suck. 

“That’s it, sweetheart. Get it nice and ready for your pussy.” Sam praised and Castiel moaned.

Castiel shut his eyes, while he sucked Sam’s finger. He opened his eyes to see Sam starring at him, mouth slightly parted, breathing heavily. Castiel’s back arched, god Sam was so sexy. 

“That’s a girl” he cooed.

Sam pulled his finger out and Castiel bent his knees. Sam rubbed the wet finger against Castiel’s greedy hole. He felt Castiel relax and Sam pushed his finger in. 

“What a tight little pussy you have.” Sam whispered.

“Uuuhhh” Castiel breathed out. 

Sam moved his finger in an out, feeling Castiel relax more. Sam wrapped his mouth around Castiel’s cock again and sucked and fingered him. The moans that were coming out of Castiel were making him hard. He knew that people might be able to hear them, but he didn’t care and coaxed those cries and moans from his boyfriend, his sub. 

Castiel screamed, voice hoarse and he came in Sam’s mouth. Sam kept pumping his finger in and out, bringing him down. Sam pulled his finger out and sat back on his heels looking at the wreck that Castiel is. Makeup running down his face. 

“What a good girl. I’m going to get you all nice and cleaned up.” 

Sam got the glove off and quckily grabbed a warm wash cloth. He wiped Castiel clean and put the cloth down and pulling up the panties.

“How was that, sweetheart? Worth the wait?”

“Ye-yes” Castiel said still trying to catch his breath. 

“Okay, baby doll, let me hold you.”

“Sir, can I take care of you?” Castiel asked sitting up and Sam shook his head, smiling. 

“Would you like to stay like that this or get comfy?” 

“I would like to wipe my makeup off, take the heels off, put on sleep shorts.”

“Yes, baby girl, that’s fine.” 

“Can-can I call you Sam? Even though I’m in panties and my crop shirt and shorts?”

“Tell you what, sweetheart. When you are wearing makeup, you call me sir. However if you just want to wear your panties and clothes, but no makeup or heels, you may call me Sam.” Castiel nodded.

Castiel stepped out of his heels and slipped on his pink plaid sleep shorts and walked to the bathroom, laughing a bit at his makeup. He wiped that off and walked back out. 

“There’s boyfriend.” Sam smiled and Castiel did too.

“I like the sound of that.” 

Castiel walked over and straddled Sam. Sam placed his hands on either side of Castiel’s face and placed little pecks on his lips. 

“I’m so proud of you, baby. You were amazing.” Sam whispered.

“Thank you, Sam.”Castiel rested his head on Sam’s shoulder and Sam held him close.


	7. Officer Winchester

**Notes for the Chapter:**

> Two in one

Castiel decided to do the whole nine. He started with a shower. Then he pulled on the black lace panties, fishnet tights and booty shorts. He zipped up his Thigh high boots and put on his leopard print corset. 

Then he did a cat style eyeliner, mascara and laid on the bright red lipstick. Then for an added touch clip no hoop earrings. 

Sam was in the other room in his cop uniform, with the handcuffs. They talked it over and Sam bought a tall cage that surprisingly fit in their closet. He waited for Castiel to knock on the door to start the scene. When he heard the knock he opened the door and took in the sight. 

“Evening officer.” Castiel ran a finger down Sam’s chest.

“Miss Novak.” Sam gripped his arm tightly.

“Oh, come on, don’t you want to have a little fun.” Castiel patted his eyelashes. Sam gripped both of Castiel’s wrists.

“You think this is funny, bitch?”

“You want a lap dance? Are you going to restrain me?” Sam turned Castiel around slipped the cuffs on Castiel. “Oh, kinky.”

“Public intoxication is a serious misdemeanor. Because of your actions and the lack to cooperate, I’m going to have to strip search you.” 

With a hand tight on the cuffs and firm on his shoulder Sam walked Castiel over to the desk and shoved him down so he was bent over.

“Don’t move” he growled in Castiel’s ear and he felt himself get hard. He heard the sound of Sam placing the latex gloves on. Castiel gave him a cheeky smile, wiggling his hips.

“Going to spank me, officer?”

“You shut your slut mouth.” He barked. 

Sam gripped Castiel again and pushed him down so he was sitting down. 

“Open your mouth.” Sam said adjusting the gloves. Castiel didn’t. “Are you stupid? Is that what it is? You’re a dumb slut?” Castiel just smirked. 

Sam pinched Castiel’s nose and tilted his head back. Castiel opened his mouth and Sam felt around. He placed two fingers in and stuck them all the way back. He pulled out and removed his hand.

“No gag relaxes. Impressed? I may be a stripper, but I do some extra work on the side” Castiel winked.

Sam gripped his chin forcing Castiel’s mouth open. He turned on a small flashlight and shown it in. Sam put the flashlight away and felt around his mouth again, this time a little more roughly. 

Sam then knelt down and took off Castiel’s thigh high boots. He pulled him up by the arm and bent him over the table again. He forcefully pulled down the booty shorts. Tights and panties. 

“Mmm, making me all wet.” Castiel spoke.

“Going to shut you up. Lift” he commanded and Castiel did. He was fully naked now. 

Sam bunched up the panties and brought them to Castiel’s mouth. He looked for approval and Castiel let out a moan. Sam pinched his nose again and shoved the panties in his mouth.

Sam reached over and grabbed the lube, popping the cap. He poured some on Castiel’s hole, which made him yelp. Sam held Castiel down with one hand between his shoulder blades. With this other hand, he circled Castiel’s hole. He pushed his finger in and felt around. Sam slid two fingers in.

“Need to make sure your pussy is all clear.” 

Sam felt around and found Castiel’s prostate and rubbed it.

“MMMPH” Castiel cried out.

Sam’s hand that was between Castiel’s shoulder blades moved to his head, to hold it to the table. Castiel felt Sam lean over him and his hot breath in his ear.”

“Need to make sure you’re not a dirty slut.” Castiel moved his hips wanting more. “Stay. Still.” He growled. 

He could feel Castiel clench around his fingers. Sam pulled out and Castiel let out a whimper. Sam removed his hands and quickly changed the gloved hand that was in Castiel’s ass.

“Pussy was clear. Need to test your clit.” Sam’s hand was back holding Castiel’s head down and Sam reached under and rolled Castiel’s balls before feeling his small erection. 

He gave a few pumps. Castiel was a crying and needing release. Sam pulled Castiel up and brought him over to the closet. He released the cuffs and cuffed his hands in front of him and Sam shoved Castiel in and locked the cage. 

“I think a night in here will do you some good.” Castiel clung to the cage.

Sam looked at Castiel, panites as a gag, corset still on, hands cuffed. Tears down his face, cock hard, him wanting more, makeup smudge. Sam left grabbed his clothes and went to the bathroom to change. 

When Sam walked back in he quickly unlocked the cage and the cuffs. He helped Castiel down. He gently removed the panties from his mouth and stroked his cheek.

“How was that, baby girl? Are you okay?” he whispered.

“Ye-yes, sir. That was perfect.” 

“And you’re okay?” he asked again and the older man nodded.

“Yes.” 

“You looked amazing. You played your part so well.” 

“So did you, sir.” Castiel smiled.

“Please go wash up, I’ll be waiting for you.” Sam kissed Castiel.

“Sir, please. May I cum?”

“I’m sorry, you will not be cumming tonight. Do you understand?” Castiel squeezed his eyes shut, trying to hold back the tears and nodded. “You did nothing wrong. You were so perfect.”

“Yes, sir. Thank you, sir.”

Castiel got his sweatpants and got out of the corset. He pulled his sweatpants on and took the earrings off. He folded up his clothes and walked to the bathroom to take off his makeup. When he came out, Sam was on his bed. He opened his arms and Castiel curled up to his boyfriend. 

“That was amazing baby.” Sam whispered.

“Thank you for making my fantasy come true.”

“You’re welcome.” Sam slid his hand down Castiel’s pants and felt that he was still hard. He pulled Castiel’s pants down, reached over, placed a towel down and started to stroke him. “Shhh. I’m going to let you cum. You were so good for me. Just relax, sweet boy. I got you.” 

When Castiel came, Sam made him lick his hand clean. Sam cleaned him up, washed his hands and got Castiel in his sweatpants. 

“Can I sleep with you, tonight?” Castiel whimpered.

“Yeah, Castiel. You can stay in my bed. I’ll keep you safe.” 

“Sam?”

“Yeah, baby?”

“I-I love you” they hadn’t said that to each other yet. Sam held Castiel tighter and kissed the top of his head.

“I love you, too.”

**Notes for the Chapter:**

> Anything you want to see?


	8. Sweet and simple

**Notes for the Chapter:**

> Simple, but sweet.

Castiel groaned when his alarm when off. He heard the snapping of a latex glove and he smiled a bit.

“Love that this is getting you excited, baby.” Sam whispered. “Alright. Pants down. Need to get that plug in.”

“Who allowed 8am classes?” Castiel whimpered. He smiled when he felt Sam’s ungloved hand stroke his cheek.

“It’s dumb, that’s for sure. Elbows and knees sweet boy.” 

Castiel pulled his pants down and rolled over, spreading his legs. Sam gave him a spank. He heard the click of the cap and felt a gloved finger rub his ass. Sam inserted his finger opening him up. He added more lube and inserted a second finger. 

“You’re going so well for me.” Sam praised. Pulled his fingers out, lubed the plug and inserted it. “There we go.” He took the glove off and smacked Castil’s ass. “You’re mine.” He whispered in Castiel’s ear. Castiel stood up and kissed Sam. 

“I love you, Sam.” he whispered.

“I love you too, Castiel. You’re so perfect.”

Castiel got dressed and went to class. Sam had the day off, so he got to study. He wondered what he could do next with his pretty girl. When Castiel came back into the room and sighed. He got undressed, grabbing black lace panties putting them on, he put on his pink t-shrt crop top and heels.

“What’s wrong baby?” Sam smiled a bit. He loved that Castiel would just go get changed now.

“Nothing. Just thought I should have skipped class.” 

“And why is that?” Sam stood up and caressed Castiel’s side.

“Just wanted to be here with you, Sam.” Sam kissed his lips. 

“I couldn’t wait for you to come home.” 

Sam snaked his arms around Castiel’s waist and cupped his ass. He placed little pecks on his lips. Castiel rested his head against Sam’s chest, arms bent, and hands on chest too. Sam placed his head on top of Castiel’s and held him close. The two stayed liked that for a few minutes. 

“This is nice.” Castiel finally whispered.

“Yeah.” Sam smiled placing a kiss on top of Castiel’s head. 

“Can you hold me? I can take a short nap before I put makeup on?” Castiel asked looking up at Sam.

“Of course, baby. I would love that” 

Sam kissed his lips and led him over to the bed. Castiel slipped his heels off and climbed into bed. Sam climbed in after him and spooned him.

**Notes for the Chapter:**

> I am in love with how sweet Sam is. Yes..I know, I wrote it. 
> 
> Anything you want to see?


	9. Bad girls shouuld be punished

It was almost time for Christmas break. Sam and Castiel were the only few left on their floor. Castiel woke up and saw Sam sitting there with coffee.

“Sam.” Castiel smiled.

“You slept in. You’re deserved too.” Sam smiled handing his boyfriend coffee.

“Thanks.”

“You got home late.” 

“Yeah, sorry about that. Did I wake you?” Sam nodded.

“You did.”

“Well…maybe…daddy’s good girl should be punished?” Castiel whimpered not sure how Sam would react.

Sam smiled, placing his coffee down and stood up walking to Castiel and cupping his cheek.

“Mmm….I think you’re right. Go get ready” Sam kissed his lips.

Castiel grabbed a floral dress, pink panties, his black heels and headed to the bathroom. When he was ready, he opened the door and saw Sam standing there with the ball gag in his hand.

“Baby girl, daddy is very upset that you got home late and woke him up.” Sam spoke firm, but calm.

“I’m sorry, daddy. I should be punished.”

“You’re right.”

Sam walked over and stroked a finger down Casitel’s cheek. He lightly patted it and Castiel opened his mouth. The ball gag was put on and secured. Sam stroked Castiel’s cheek. 

“Over my knee, baby doll. You need a spanking.” Castiel whimpered.

Sam led Castiel over to his bed. He sat down and guided Castiel over his knee. Sam lifted up the dress and rubbed a hand on his ass.

“I think twenty. Hands.” Castiel folded his arms behind his back and Sam held tight. 

SMACK! SMACK! SMACK! SMACK! SMACK!

Sam alternated right and left butt cheeks. Castiel bucked his hips forward.

“You know that naughty girls get spanked. Is that why you stayed up late?”

SMACK! SMACK! SMACK! SMACK! SMACK

“That’s ten, baby girl.” Sam said massaging Castiel’s sore ass. 

He pulled down the panties and gave five more sharp, hard smacks.

“AHHH.” Castiel cried out.

“You’re a very naught girl, aren’t you?” 

“Mmph” Castiel whimpered. Sam reached forward and felt the pre-cum leaking out of Castiel’s cock.

“Baby girl, you seemed a bit excited.” Five more smacks came.

These were harder and Castiel screamed, crying now. He loved it. Sam rubbed a hand over Castiel’s Cherry red ass. Sam let go of Castiel’s arms and stroked his hair. 

He stood Castiel up. Panites dropping around his ankles. Makeup running down his face. His tiny erection making the dress poke out a bit. Sam placed his hands on either side of Castiel’s face.

“Did daddy’s girl learn her lesson?” he cooed and Castiel nodded. 

“I don’t know.” Sam bent down and pulled the panties up; he smoothed Castiel’s dress down. “Do you want to make up for your mistake?” Castiel nodded, eagerly. Sam grabbed Castiel’s pillow and placed it in the middle of the bed. “Hump your pillow.” 

Castiel nodded and straddled his pillow. He started to roll his hips and Sam came over cupping the back on his head. Castiel continued his actions. 

“You going to cum in your pretty panties, baby girl?” Castiel nodded looking at Sam with pleading eyes. “Well, reach down and show daddy how you rub your clit.”

Castiel stroked his cock through the panties and cried out, head dropping forward and spilling in his panties, making a mess. Some leaked through the lace on his pillow. 

“Good girl. What a good girl you are for me.” Castiel whimpered. “Aww, panites a little sticky?” Castiel nodded, spit now coming out from the ball gag. “Are you sorry that you came home late?” Castiel nodded. Sam took the ball gag out. “Once more.”

“Yes daddy. I’m sorry. I was a naughty girl.” Sam kissed down his neck.

“Want to make it up to daddy?”

“Yes” Castiel breathed.

“On your knees then”

Castiel sank to his knees and undid Sam’s pants and pulled them down, free his hard cock. He wrapped his mouth around it. Sam ran a hand through Castiel’s hair.

“Good girl.” He purred.


	10. Trying something different

Over the Christmas break Sam and Castiel talked about maybe going out to a movie or dinner. Castiel wanted to be all dolled up and Sam loved that idea. When Sam got back to the dorm, Castiel had just shaved himself. 

“Hey baby” he smiled kissing the blue eyed man.

“Hey Sam” Castiel smiled.

“Are you excited for out date tonight?”

“Yes.”

“Good thing we’re in California, you can wear those sexy black heels I love so much.” Sam snaked his arms around Castiel’s naked body and kissed him. “Now, I bought you something. I know you’re worried if you get a little excited it’ll show with your skirt.” Sam walked over and pulled out a pink male chastity device. “We talked about this.” 

“Sam, I love it!” Castiel smiled.

“Yeah?”

“Yeah.”

“Alright, baby. Let’s get your plug in.” Sam said grabbing latex gloves.

Once the plug was in, Sam helped Castiel into the chastity device. He locked it, but put the key on a necklace and put it around Castiel’s neck. 

Castiel pulled on a skirt that was mid-thigh. black, high waisted so the belt wouldn’t show. He put on the burgundy halter top and black sweater. He slipped on the heels and went to the bathroom to put on his makeup. Sam got dressed in his jeans and a nice dress shirt. Castiel walked out of the bathroom and Sam smiled.

“Baby girl, you look so beautiful.”

“Thank you, sir. You look very handsome.” 

They slipped out the back door so no one would see. Castiel had a small purse as well. 

“I can’t wait to see the movie, sir.” Castiel smiled.

“I can’t wait for people to see how pretty you really are, baby doll.” 

“Thank you, sir.”

The boys got in Sam’s car and they drove a bit so they wouldn’t run into classmates. Sam ran his hand up Castiel’s thigh and leaving it there.

“Mmm.” Castiel smiled.

“Good thing we talked about locking you up. I’d have you do hard, people would for sure noticed with that tight skirt you’re wearing.”

“I know, it was a good idea. Thank you for being open with it.”

“Of course, baby girl.” Sam stroked his cheek. “God, you’re beautiful.” Castiel blushed.

“Thank you, sir.” 

“I have to say, I did like when you called me daddy. I’m just saying, if we did that again, I would love it.” Sam blushed now.

“Hm, good to know.” Castiel smiled.

They parked and Sam got out, opening the door for Castiel and helping him out. Sam placed a kiss on his lips. 

“You’re a pretty girl.” He whispered in Castiel’s ear.

“You’re very handsome, sir.” Castiel whispered back. Sam reached down cupping Castiel’s ass and giving it a firm squeeze. “Mine” Sam growled and Castiel let out a soft moan.

After the movie, the boys went out to a restaurant. Castiel braced himself for gasps and whispers, but no one said anything. Sam guided Castiel with hand on the small of his back. 

When they got back to school there were some people around. Castiel blushed and looked down. Sam wrapped his arms around his waist.

“Baby doll, I know. But we can quickly get inside.”

Castiel nodded and the two walked in. Thankfully no one noticed and they got into their room. Sam locked the door and kissed Castiel passionately.

“What a good girl you were today. Everyone saw how pretty you were.” 

“Yes” Castiel smiled. 

“I think we need to have a talk.”

“Did I do something wrong?” Castiel asked worriedly.

“No, baby girl. We’ve been taking things slowly. I think tomorrow I should fuck your pretty pussy? What do you think?” 

“Yes, sir. I would love that.”


	11. Eating out

Castiel was all dolled up. Ball gag in his mouth, pink sundress on and black panties on. He was on his elbows and knees. Sam snapped on latex gloves and pulled down Castiel’s panties, pulling it out.

“Going to clean you out first, baby girl.” 

“Mmph” Castiel lowered his head when he saw Sam place the enema bag on a hook. 

He heard the popping of the cap and a gloved lube finger rub against him. Castiel took deep breaths and Sam pushed his finger in.

“Good girl.” He praised, he worked two fingers in and then pulled out, lubing up the nozzle and inserting it. “I’m going to start the water. Deep breaths.”

Sam started the water and took his gloves off. He lightly massage the cramps in Castiel’s stomach. Once all the water was almost empty, Sam put gloves on again and lubed up the plug. He pulled the nozzle out and pushed the plug.

A few minutes later Castiel was able to release and he was happy. Donning new gloves, Sam placed his hands on either side of Castiel’s face and kissed his ball gag.

“On your back, baby doll, legs spread.” Castiel did and he watched Sam squeezed lube into his hand and start to stroke his own cock. “Hook your knees over your arms. Show me your greedy pussy.” 

Castiel did, moaning. Sam grabbed more lube and rubbed it against Castiel’s hole. Castiel spread his legs more when Sam pushed a finger in him.

“That’s a girl” Sam praised.

He worked Castiel open more and then took his gloves off ad lined himself up slowly pushing himself in. They hadn’t done this before so he wanted Castiel to be comfortable. Castiel bucked his hips and Sam ran a hand on his inner thighs.

“So needy, aren’t you pretty girl.” Sam smirked. 

Castiel’s head dropped back and his back arched when Sam started moving. It felt so good and strange. He was bigger than his last dom. But Sam was also his boyfriend and so this was different, this was with love. Sam reached down and started to stroke Castiel’s cock.

“Mmm, your clit is so responsive tonight.” Sam looked at Castiel, ball gag in his mouth.

Sam stilled and his hips and Castiel whimpered. He took the ball gag off and kissed Castiel’s lips.

“Sir, please! Please! I need more.”

“You’ll get it, baby girl.” Sam stroked his cheek. 

Sam felt Castiel clench around him. Sam lifted up the dress and sucked on one of Castiel’s nipples. Castiel was shaking, trying to keep his legs open.

“Oh god, yes!” Castiel cried. 

The sensation of Sam’s lips on his nipples, hand on his cock and his cock in his ass was amazing.

“Yeah, you liked that, I know what else you will like.”

Sam pulled out and had Castiel let go of his legs. Sam knelt in front of Castiel, hands sliding under his ass. He licked his lips and then started to lick Castiel’s ass.

“Yes! Yes! Sir!” Castiel yelled not caring if anyone heard.

“Mmm, your pussy taste good.” Sam mumbled before going back and licking.

“NAAA” Castiel came, panting. 

“Good girl. Good girl.” Sam praised.

He got up and slipped on latex glvoes. He walked over to Castiel who sat up and grabbed his chin and opened Castiel’s mouth. Castiel looked up and Sam smiled. He gave a few pumps and came in Castiel’s mouth.

“Now you hold that there for ten minutes. Hmmm. Can you do that for me.” Sam leaned down to whisper in his ear. “Can you do that…for daddy?” Castiel nodded.

Sam stroked Castiel’s cheek and sat watching his good girl sit there patiently. Once ten minutes were up Sam stood up and walked over, kissing Castiel’s forehead.

“Swallow.” He whispered and Castiel did making sure he got all of it. “Now open your pretty mouth. Nice and wide for me.” 

Castiel opened his mouth and Sam felt around. He pulled his fingers out and brushed his gloved thumb against his lips. Castiel opened his mouth and sucked on the thumb.

“Good girl.” Sam smirked.


	12. Yes daddy

“Sam?” Castiel asked. 

They were both writing essays for school. Castiel was in pink lace panties and nothing else. Sam was just in his sweatpants.

“Yeah, baby?” Sam looked up.

“Can we have a talk?” Castiel placed his laptop down.

“Of course. Castiel, are you unhappy?” Sam asked concerned and he shook his head. Sam placed his laptop down too.

“I-you said you liked me calling you daddy and I liked it too.” Sam cracked half a smile.

“Yeah?”

“Yes. I know I call you sir, but I would like to call you daddy…if that’s alright.”

“That is very alright. Sweet boy, come here.” 

Castiel wasn’t in make-up. He stood up and walked over to Sam, who also stood up. Suddenly he felt so small next to him. Sam cupped his cheek and kissed him softly. 

“Sir or daddy is fine by me. Gabriel and I went a whole month with him calling me daddy.”

“Really?” Castiel looked excited.

“Yeah. In fact that’s what he calls Dean. Daddy and sir.” 

“I-I would like to call you daddy. I want to be daddy’s good…boy.” Castiel looked down and Sam lifted his chin.

“We have been having a lot of sex with being you being a good girl. We haven’t had a lot of us time. I’m sorry for that. Let daddy make it up to you, sweet boy.” Sam whispered. Castiel nodded.

“Yes, daddy.”

Sam gently kissed Castiel and then trialed kisses along his jaw and down his neck. Sam guided Castiel back against his bed. He gently laid him down, kissing back up to his lips. 

“I’m going to take it real slow, okay? Is that oaky, baby?” Sam whispered against his ear.

“Yes, daddy.” Castiel breathed out.

“Okay, going to put the gloves on.” 

He placed a quick peck to his lips and got up, grabbing the gloves and lube. He took his sweatpants off and put the gloves on and climbed back on top of Castiel, caressing his cheek and looking at the blue eyes staring back at him. He kissed down Castiel’s neck, nipping at his pulse point. A gloved hand found its way to Castiel’s neck and started stroking it, causing the older man to shiver. He rested the hand on the base of his throat, returning to his lips to give soft pecks. 

“You’re a good boy.” He whispered, grinding done making Castiel moan. “My good boy”

Sam kissed down his chest and then pulled the pink panties off. He kissed back up and brushed two fingers against Castiel’s lips. Castiel parted his lips and sucked on the two gloved fingers. Castiel closed his eyes and listened. When he sucked on Sam’s fingers Sam would part his lips and breathe. The heavy breaths is what gets Castiel hard.

Sam’s slow steady breathes and him rubbing his cock against Casitel’s cock made his back arch. He sucked on Sam’s fingers needy and hungry. 

“Yeah, good boy. Getting them all nice and wet for me.”

Sam pulled his fingers out and rubbed them against Castie’s hole. Castiel let out a low moan and relaxed, allowing the two fingers to sink into him. Sam moves his fingers in and out

“Please, daddy” Castiel moaned. 

“Need to open you up” Sam whispered, scissoring his fingers. He hit the bundle of nerves, rubbing against Castiel’s prostate.

“OH!” Castiel bucked his hips 

“Ah, there we go.” Sam smiled.

Sam started to stroke himself with this other hand and Castiel gripped the sheets and shut his eyes whimpered at the loss of Sam’s fingers when he pulled out. He heard the popping of the lube cap and Sam’s tip pushing at his hole.

“Mmm, I need you.” Castiel whimpered.

“I know, sweet boy.” Sam pushed all the way in, took the gloves off and leaned forward, kissing Castiel’s lips.


	13. Sick boy

Castiel was coughing all night long and he hated the he woke Sam up. In the morning Sam got dressed to get some supplies for the day. He placed a hand on Castiel’s forehead and frowned. He was burning up. Sam left the room to get medicine and things he needed. When he came back Castiel was sitting up coughing. 

“I don’t want you to get sick.” Castiel coughed. 

“I got that covered.” Sam placed the stuff he put on his bed and pulled on latex gloves and a medical mask. Castiel whimpered. “Castiel, I wish you would go to the doctor.”

“I-I don’t like doctors” Castiel said through coughing.

“Well I spoke to our neighbor Jess. I can give you an exam.” Castiel tried to smirk a little “Sweet boy, not what I meant.” He soothed.

Sam felt around Castiel’s neck. He nodded and grabbed a little flashlight that he had and a tongue that he bought.

“Sam” Castiel looked up at him a little annoyed.

“Baby, if you wont go to the doctor, I’m going to examine you myself.”

“You’re in school for law.”

“I’ve been helping Jessica study from time to time. Now open your mouth, please”

Castiel did and Sam Sam looked in his mouth. He threw the depressor out and put the flashlight down and picked up the stethoscope and placed the buds in his ears and placed it on Castiel’s chest.

“Nice deep breath for me.” Sam said.

Castiel did and let out a cough. Sam placed the stethoscope on his back. Castiel couldn’t help but be a little turned on by this. Sam looked sexy like this. Sam put the stethoscope down and had Castiel laydown. His nose was running too.

“Great, can I go to bed now?” Castiel coughed.

“I’m going to need to take your temperature.” Sam said.

“Just give me the medicine and let me sleep.” Sam crouched down and stroked Castiel’s cheek. 

“Baby, I know you’re not feeling well, but before I left this morning you had a fever.”

“I’m sorry” Castiel started to tear up. He always got a little weepy when he was sick.

“Oh, sweet boy you don’t have to be sorry.” Castiel nodded.

“Just going to put some Vaseline on your nose, okay?” Sam said grabbibng the Vaseline.

“Okay.” Castiel whimpered.

Sam opened the jar and got a little on his finger. With this free hand he held Castiel’s chin lightly and rubbed the Vaseline on his nose. 

“Good boy. I’m going to take your temperature now.” Castiel opened his mouth for the thermometer. Sam stroked his cheek. “I’m sorry, baby. I’m going to need an accurate reading. Roll on your other side for me.” 

Castiel groaned as he rolled over. He felt Sam pull his pants down. He heard the popping of the cap and a lube finger brush against his hole. Sam spread Castiel’s cheeks and slipped the thermometer in

“101.7.” He placed down and changed his gloves. He pulled Castiel’s pants up and had him roll over to face him. “I’m going to give you some medicine for your fever and cough. If that doesn’t help, I’ve got some suppositories that will help.” Castiel whimpered and Sam grabbed the vapoRub and rubbed some on Sam’s chest.

“Thank you, Sam.” Castiel whispered.

“You’re welcome baby.” He cooed.

Sam changed that glove and poured the medicine and handed it to Castiel to take. When he did, Sam held water up for Sam to take.

“Class” Castiel got out.

“I know I have class today, but you need to be taken care of.” 

Sam kept the mask and gloves on. He changed into his sweatpants and watched as his boyfriend fell asleep. Castiel coughed a bit, but eventually he was out. An hour later he woke up and Sam was wiping Castiel’s face with a wet cloth

“How are you feeling, baby?” Castiel whimpered. “Okay, I’m going to take your temperature again.”

“Not in my bum, please.” Castiel whispered.

“I’m sorry, sweet boy.” Sam said placing the cloth down. 

Castiel rolled over and Sam lowered the older man’s pants and rubed his hole and slid the thermometer in. A few minutes later Sam pulled it out and frown a bit.

“Ev-everything okay?” Castiel whimpered. 

“It’s gone up a bit, baby. I’m going to give you other medication.”

Castiel heard the crinkling of the foil and Sam’s lubed finger work its way in his ass. Then Sam placed the bullet shaped pill against it and pushed it in. He held it there. He inserted the other one and held it.

“Sa-Sam, this wont make me…”he trailed off.

“No, Castiel. These are strictly for bringing down a fever, not for bowel movement.” Sam changed his gloves and pulled Castiel’s pants back up. I’m going to grab you some soup from the cafeteria, okay, baby?” 

“Okay, thank you” Castiel whimpered.

“I love you so much.” Sam whispered.

“I love you too.”


	14. Taking care of his baby

**Notes for the Chapter:**

> There will be a third part to this.

When Sam returned with the soup he smiled seeing Castiel sitting up. He put on a new mask and gloves and grabbed a towel, placing it over Castiel’s chest like a bib.

“I’m glad you’re sitting up. I have some soup for you.”

“Looks good” Castiel coughed a bit.

Sam fed Castiel the soup, giving him some water. When Castiel was full, Sam grabbed the Vaseline and Castiel groaned turning his head away.

“I know it’s yucky, Castiel, but it helps.” 

“Mmm” he whined. Sam lightly gripped his chin again and rubbed the Vaseline on. 

“Castiel, I think the best course of action is to strip you of your clothes completely. Just a thin layer of blankets.”

“Nnnnn.” He whined.

“Castiel, it will be easier to administer your medication and take your temperature.” Sam said starting to strip his sheets.

“Please” Castiel whimpered, starting to tear up. “I’ll be a good boy.” 

Sam paused at that. He sat on the bed and stroked Castiel’s cheek with one hand and took his wrist and pressing at his pulse point. He looked at his watch.

“Baby, I know you’ll be a good boy. You’re always a good boy for me. Hmph. Pulse is a little fast. “ 

“I’ll be a good boy sir.” he cried. Sam felt his heart sink. He stroked his cheek and ran a gloved hand through the blue eye man’s hair.

“Oh, Castiel. You are a good boy. You are. You’re my good boy. Such a good boy for me. I just need you to get better. Otherwise I need to take you to the doctor.” 

“No!” he cried out, grabbing onto Sam. “Please, not the doctor. I don’t want that. Please.” He started coughing, shrinking into himself and curing in a ball.

This must have been because of his old master. Something must have happened when he was sick and with a doctor that scared Castiel. Sam placed a hand on Castiel’s chest and cupped his cheek.

“Baby, can you hear me?” Sam whispered and Castiel nodded. “Good boy. Can you look at me?” Tear filled blue eyes looked up at him. “Good job. I won’t hurt you, sweet boy. I won’t hurt you. I just want to make you feel better. I want to bring your fever down, give you more medicine and let you rest up.” Castiel nodded. “Yeah? I can do that?”

“Ye-yes, sir.” Castiel whispered.

“Not sir, it’s Sam or daddy.” 

“Daddy?” Castiel whimpered and Sam nodded.

“I’m going to take care of my sweet boy.” Sam whispered and Castiel nodded. “Okay. I’m going to get you out of your pants. Then, I’m going to lay you on the ground for a moment while I strip your sheets, get you nice clean ones. While that’s happening I’ll be taking your temperature, okay sweet boy?”

“Yes daddy” 

“Good” Sam cooed.

Sam laid a duvet on the ground with some pillows by his bed. He got Castiel out of his pants and lifted him up, lowering him to the ground. Castiel was crying the whole time and Sam did nothing but soothe him. He lubed up his finger and rubbed it on his hole before sliding in the thermometer. He changed his glove and covered Castiel up with a thin blanket.

Sam got to work stripping Castiel’s sweat soaked sheets and putting fresh ones one. He placed a long towel down on the bed. He looked over when Castiel whimpered and Sam went over and bent down, pulling the thermometer out.

“Oh, good boy. 101.6. You got it down.” Sam put the thermometer away. Sam lifted Castiel up and placed him back on the bed. He covered him up with the sheet. “Baby, I’m going to be right back okay? Going to give you a nice sponge bath.” Castiel nodded

Sam filled two buckets with water. One with soap and one plain. He carried them out and grabbed a few cloths. Sam wet the cloth and got to work.

“Alright, baby. I’m going to wash your face first.”

“Yes daddy” Castiel whimpered.

Sam carefully washed his face, ears and neck with the soapy water. He then rinsed it and dried with a towel. He then carefully was Castiel's arms and shoulders. He lowered the sheet and washed his chest. He dried it and placed the blanket back over.

“Just going to change the water, sweet boy. You’re doing very well.” 

Sam changed his gloves and changed the water. He came back and rolled Castiel over. He whimpered a bit.

“Shhhh, baby. Just going to wash you back. Now medicine yet.” 

Once his back and butt were washed he spread his butt cheeks and cleaned there. He washed his gentile area and little cock. He then changed his gloves again and Castiel heard the crinkle of the foil. Once the medication was inserted Castiel was rolled on his back again.

Sam noticed that Castiel was relaxed and started to drift off to sleep. He hoped his boyfriend would be feeling better soon.

**Notes for the Chapter:**

> ideas?


	15. Getting better

The next day was much the same. Though Castiel was feeling better Sam still insisted of taking his temperature rectally and giving the suppositories. He still work the gloves and mask. It was Saturday so no one had classes. Sam got Castiel dressed in his sweatpants. He ran a hand through his hair.

“Baby how are you feeling?” Sam asked. 

“Better Sam, thank you so much for taking care of me.” He whispered.

“Of course. That’s what boyfriends do.”

“Plus, you look really sexy like that.” Castiel confessed blushing. Sam blushed as well.

“Thank you. Now, I think we need to talk about maybe taking you to get a flu shot, next time.”

“N-no. No. Sam, I can’t. I can’t do that. “ 

“Baby, what happened with the doctor?” 

“I-I can’t.” Castiel whimpered.

“You’re safe, you’re safe.” 

“My dom…he made me get a flu shot, he took me to a doctor and made me get one. It made me so sick. I didn’t want to play with him one day, I wasn’t feeling well. The doctor came and my dom had me strapped to a table while the doctor put and IV in me. Get me” Castiel started coughing a bit and Sam stroked his cheek. “Get me hydrated and my dom fucked my ass. Told me to be a good patient and take my medicine. The doctor…his brother fucked my throat.” Castiel started crying and coughing. 

“Castiel, I-I’m so sorry.” Sam had tears in his eyes now. 

“They did that every time I got sick. Gave me an IV. That’s why I hate going to the doctors. Why I hate needles.” 

“Okay. Baby, thank you for telling me that. You’re a good boy. Such a good sweet boy.”

“Than-thank you for being kind. For being a real dom.” 

“You’re very welcome, baby. Now rest your eyes. Daddy is going to take care of you, okay?” 

Castiel did not argue. His eyes fluttered closed. He felt Sam’s hand grip his chin and he whimpered when the Vaseline was rubbed on his nose. He sighed when he felt the VapoRub on his chest.

When Castiel woke up from his short nap, Sam was reading. He smiled at the older boy and walked over.

“I feel a bit better” Castiel coughed.

“Good. I got some Gatorade. Here.” Sam held the bottle up to his mouth and Castiel drank. “Good boy. Going to check you out a bit.”

Sam helped Castiel sit up. He felt around his neck again. He grabbed the flashlight and another tongue depressor and Castiel opened his mouth. 

“Good. Swelling has gone down.” Sam threw the tongue depressor away and took Castiel’s wrist and felt his pulse. “Normal pulse. Much better than yesterday.”

“I have a-a good nurse.” Castiel smirked

“Yes you do.”

Sam listened to his heart and lungs. He helped lay Castiel down and pulled his sweatpants down. Castiel groaned when he felt the thermometer go in.

“There we go. Few minutes baby.”

“Sam?” Castiel whispered.

“Yeah?”

“I-I would like to meet your brother and Gabriel. If that is okay. If not, I wont mind.”

“I think that’s a wonderful idea. I know Dean wants to meet you. So does Gabriel.”

“Do-do they know?...about the panties and the feminization?”

“No, sweet boy. I didn’t tell them that. Not without your permission first.” 

Sam pulled the thermometer out and got the suppositories ready. He lubed it and pushed it in holding it there.

“Relax, sweet boy. I know, this is uncomfortable, but it’s making you much better.”

Once the second suppository was in, Sam pulled the sweatpants back up. 

“Sam, I have to go to the bathroom.” Castiel whimpered.

“Would you like to try and stand to go, or do what we did yesterday?” 

Castiel sighed. Yesterday was a little fuzzy, but he knew that when he had to go to the bathroom Sam held up a bedpan jug. It fit right over his little cock. 

“I’d like to try and stand.” He replied.

Sam helped Castiel sit up slowly. Castiel wrapped his arms around his boyfriends neck and Sam slowly stood him up. Castiel was shaky and got a little lightheaded. Sam steadied him. 

“Would you like to continue?” Sam whispered.

“No-No. Sorry, I’ll just use the bottle. Sorry.” Castiel said.

Okay, baby.” 

Sam wrapped his arm around Castiel’s waist and pulled down his pants. He lowered Castiel and grabbed the bedpan jug, guiding his cock into it. Castiel was a little more award of the situation today.

“It’s alright. I did this yesterday.” Sam soothed and Castiel closed his eyes and let himself pee. “Good boy.” 

Sam moved the bottle away and grabbed the baby wipes wiping Castiel clean. He helped Castiel back in his pants and helped him to bed. 

Sam went to dispose of the pee in the toilet and came back changing his gloves. He gave Castiel some more water and then returned to studying.

**Notes for the Chapter:**

> I will now be working of adding Dean and Gabriel


	16. A vistit from Dean and Gabriel

Two weeks later Castiel was better. Sam had called Dean and the boys were coming to visit them at the dorm. 

“Now, baby what would you like to wear?” Sam asked Castiel. 

“Would they mind…if…I were…uh…in panties?” Castiel looked down and Sam stroked his cheek.

“No. They wont mind. I bet, if you wanted to get all dolled up, that they would love it.”

“If I wore my pink lace panties and a black crop top, with heels.”

“No skirt?” Castiel shook his head. “And your face would be all dolled up?” Castiel nodded. “They would love it, baby.” Sam kissed Castiel’s forehead.

“What about my small penis? It makes me embarrassed.” 

“I know it does, but you don’t need to be. Besides.” Sam got close to Castiel’s ear “It’s a pretty little clit.” Castiel moaned and nodded. “The boys will be here soon, baby, go shower and shave. Get ready to meet them.”

“Yes, sir.”

Sam heard the shower run a few minutes later there was a knock on the door. Sam opened it and smiled seeing his old sub and his brother. Gabriel had a nice thin black collar on. The boys stepped in.

“Sammy” Dean smiled hugging his brother.

“Dean. Gabriel, you look amazing.” Sam smiled.

“Thank you, Sam.” Gabriel smiled. Dean cleared his throat and Gabriel blushed taking his sweatpants and t-shirt off. 

“Oh, is someone being punished?” Sam asked seeing the golden eyed man in a diaper.

“Yes he is. He misbehaved, didn’t you sweetheart?” Dean asked rubbing a hand on Gabriel’s head.

“Yes, daddy. I’m sorry.” Gabirel looked down. 

“So, where is your beautiful sub?” Dean smiled.

“Castiel is getting showered.” Sam lowered his voice. “He’s going to be all dolled up” Sam let them know ahead of time with Castiel’s permission that he would be Sam’s good girl. “Now, he’s a bit nervous. Because he cock is small.”

“How small” Gabriel asked.

“Two inches.” Both men raised their eyebrows and shrugged.

“That’s nothing to be embarrassed about.” Dean said. 

“Sam, I’m really glad that things have worked out for you.” Gabriel said, holding onto his hand.

“Thank you, Gabriel. I’m very glad you and Dean have made it official.” Dean leaned over and kissed the side of Gabriel’s head. 

“Let me go check on my girl.” Sam smiled.

Sam knocked on the door and came in. 

“Aww, baby girl, you look beautiful.” Sam smiled 

“Thank you, sir. “

“They can’t wait to meet you.”

“I’m ready sir.” Castiel smiled.

“Good girl” Sam praised.

“Now, Gabriel is being punished okay? Remember that.” Castiel nodded. 

Sam linked fingers with Castiel and they walked out of the bathroom. Dean was changing Gabriel’s diaper. That was part of the punishment. 

“Sweet girl, this is my brother Dean and Gabriel.” Sam spoke. 

Dean did the diaper up and took the latex gloves off and helped Gabriel stand. Both men smiled at Castiel.

“Hi” Gabriel said.

“Hi” Castiel blushed a bit.

“Don’t you look pretty.” Dean smiled 

“Thank you…” Castiel didn’t know what to call him.

“Dean, pretty girl. You can call him Dean” Sam said.

“Castiel, my beautiful sub is in the middle of a punishment. Would it be okay if I continued? If not, that’s very okay.” Castiel blushed and Sam pulled him close.

He had asked Castiel if it was okay to share with Dean and Gabriel what his old dom did. Castiel nodded, said that it was important.

“We’re very open.” Gabriel explained. “However, we do not want to make you feel uncomfortable.”

“What would he have to do?” Castiel whispered.

“Well, daddy’s good boy is to warm my cock. Isn’t that right?” 

“Yes, daddy” Gabriel smiled.

“It’s okay” Castiel smiled. “I’m okay.” 

“Okay. Thank you, Castiel.”

Dean undid his pants and Gabirel got on his knees. He ran a hand through the blond hair, to soothe his sub. Sam turned to Castiel and stroked his cheek.

“Baby girl, did you want to dance for us. Like how you did for me? “

“Yes sir.” Sam kissed his lips.

Sam sat down and Castiel started to dance. Dean and Sam smiled at each other. They had good subs.


	17. Continuing the visit

“Okay, baby boy. Suck” Dean told Gabriel who was still warming his cock. Castiel was still dancing for the boys.

“Do you want to suck something baby girl?” Sam asked Castiel.

“Yes, sir.” Castiel cooed. Sam reached over and grabbed a latex glove and put it on.

“Come here, sweet girl” Sam smiled beckoning Castiel over with two fingers. 

Castiel walked over to his dom and Sam had Castiel kneel at his feet. He brushed two fingers against his lips and Castiel parted them, taking them in and sucking.

“You got a beautiful sub, Sammy.”

“I sure do” Sam smiled at Castiel. “How long is Gabriel going to be punished?”

“Another week.” Dean said, cupping the back of Gabriel’s head. “Slow it down” he said to his sub and Gabriel slowed it down.

Sam’s warm hand wrapped around the back of Castiel’s neck. Castiel still happily sucking the gloved fingers. Sam leaned forward and Castiel moaned at the hot breath in his ear.

“Can we show Den you’re pretty clit? You can say no” he pulled back and Castiel nodded. “Yeah?” he whispered. 

He nodded again. Sam smudge a bit of Castiel’s lips stick with his gloved thumb. Sam pulled his fingers out and had Castiel stand up. Sam stood up and turned Castiel around to face Dean.

“Dean, would you like to see my pretty girl’s clit?” Sam asked.

“Sure would.” Dean smiled. Sam pulled the panties down a bit. “Wow. Very nice clit you have.” 

“It’s it perfect” With the gloved hand, Sam started to stroke Castiel a few times and then pulled the panties back up. 

“Thank you for showing me. Alright, baby boy, make me cum.” He spoke to Gabriel.

Sam pulled the glove and kissed Castiel. The two laid down on Castiel’s bed and Sam made out with him while his brother moaned and came in his subs mouth. Dean pulled out of Gabriel’s mouth and cupped his cheek.

“You’re not going to swallow yet are you?” Dean cooed and Gabriel shook his head. “Nooo, you’re going to stay like that” Gabriel nodded.

Sam pulled off of Castiel and smiled. Sam pulled him on his lap and held him close. Dean pulled his pants back up. He patted his lap and Gabriel straddled his dom. Dean patted his diaper butt and rubbed it.

“For a punishment Gabriel is treated like a baby, unable to do things. Unless it’s out in public. He has to wear the diaper under his clothes. But if he uses it, he is taken to the little boys room and changed.” Sam whispered in Castiel’s ear, explaining. Dean patted Gabirel’s butt a few times.

“Who’s a good boy?” Dean cooed. Gabriel nestled in his neck. “Are you going to swallow for daddy?” Gabriel nodded. 

Castiel was fascinated by the whole thing. The fact that even Gabriel had to wait for permission. The willingness to be a baby. Sam cradled Castiel’s head to his shoulder and kissed the top of his head. 

Gabriel swallowed. Dean laid him down on the bed and pulled on a pair of latex gloves. He gripped Gabriel’s jaw and inspected his mouth. 

“Good. Castiel, do you think you could go in the diaper bag and grab me Gabriel’s pacifier gag?” Dean smiled.

Castiel looked at Sam who rubbed a hand on his back and nodded. Castiel got up and went to the diaper bag pulling the blue pacifier gag out and handing it to Dean. Dean placed it on his sub and did it up. He took the gloves off and lifted Gabriel up, cradling him. 

Castiel reached a hand out. He wanted to stroke Gabriel’s hair. He looked at Dean who smiled and nodded. Castiel stroked Gabriel’s hair. Gabriel smiled at Castiel. 

“Aww, you like that baby?” Dean cooed booping Gabriel’s nose. Gabriel nodded. 

“Sir?” Castiel spoke.

“Yes sweet girl.”

“I-I would like to take the makeup off and the crop top. Just be in the panties and be your sweet boy now.” Sam smiled and nodded.

“Okay, baby. You may do that. I’m going to hold you though.” Castiel smiled and nodded.

Castiel took the top off and folded it. He went to the bathroom to take the make-up off. Sam got up and sat by Gabirel’s hair, running a hand through his hair.

“Sam, we are so happy for you and Castiel. You have such a sweet boyfriend. Mom and dad would be proud.” Dean smiled. Gabriel nodded and gave the thumbs up. Both men chuckled a bit.

“Thank you. I really love him. Not that-“ Sam realized and Gabriel grabbed his hand letting him know what he meant. 

Castiel came out and Sam got up and pulled the chair out. He sat down and Castiel straddled him, resting his head on his shoulder. Sam wrapped and arm around his waist and rubbed his back.

“You’re a good boy. You were so brave today. I’m so proud of you” Sam whispered. “I love you so much, Castiel” Gabriel and Dean looked up at each other smiling.


	18. Trying something new

**Notes for the Chapter:**

> Sometimes it's nice to relax and be non-sexual.

Since the visit with Dean and Gabriel, Castiel had gotten curious about the diapers. He knew that it was a punishment, but the whole thing fascinated him.

“Sa-Sam?” Castiel asked one morning while Sam was putting the plug in him.

“What is it, baby?” Sam asked rubbing a gloved finger on Castiel’s hole.

“There’s been-oh” Castiel gasped when Sam pushed a finger in him. “Something I wanted to talk about”

“Sure.”

“The diapers, I know that Gabriel-“

“Nice deep breath” Sam said as he pushed the plug against Castiel and he did. “sorry, baby, continue.” He smiled patting his butt. Sam took the gloves off and Castiel got ready for class.

“The diapers, they fascinated me. I know it was a punishment for Gabriel…but.” Sam smiled.

“That was my idea for a punishment. Gabriel and I talked about it first, of course. He liked the idea. Dean liked it.”

“I-I would like to try wearing one.” Castiel blushed and Sam come over and kissed him. 

“Yeah?”

“Yeah.”

“Would you use it?”

“Oh! Uh?”

“I have changed Gabriel many times, that was part of his humiliation. However, if you’re not comfortable using them, that’s very okay.”

“I would like to try and use it” Castiel looked down and Sam pulled him close to his chest.

“Sweet boy, you go to cyour classes and when you come back, I’ll have everything you need.”

“Okay, daddy” Castiel responded. 

The whole time Castiel was in class he was nervous, but excited. Sam was happy that Castiel was open to this. He had a diaper bag ready if he found a sub who wanted to try. 

Castiel couldn’t get out of class fast enough. However this was his day where he had three classes in a row and two of them had tests. When he walked in he saw that Sam laid everything out.

“Wow” Castiel breathed

“I had everything ready in case I had a sub who wanted to do this. Now. Castiel, do you just want to wear the diaper or would you like me to treat you like a baby? With a pacifier, I have an attachable nipple that goes on any water bottle. It’s up to you, Castiel.”

“Like infantilism?”

“Yes, but again, entirely up to you. Castiel, I am open to whatever. It can be a onetime thing, we can try it.”

“Would there be any sexual things?”

“Only if you want. If not, that is very okay. If my sweet boy just needs to be a baby and cuddled, no sexual things at all, I would be more than happy to do that.” Sam smiled. 

“I-I would like that Sam. A non-sexual age play.” Castiel looked down.

“You got it sweet boy. Now. How were your tests?”

“Hard daddy. I just want to forget about it for a while.”

“Okay, sweet boy, let daddy take care of you.”

Sam helped Castiel out of his clothes. He placed a changing mat on the bed and helped Castiel laydown. He slipped on latex gloves and pulled the plug out. He lifted Castiels legs and wiped him with a baby wipe. 

“Can you keep your legs up like that, baby?” Sam cooed and Casitel did. “Good boy”

Sam placed a diaper under him. He opened the baby powder and sprinkled it on him. He smiled at Castiel who was looking down at the whole thing amazed. Sam did the tabs up. He took the gloves off and removed the changing mat. 

“Can daddy hold his boy?” 

“Yes.” Castiel said shyly. Without any effort Sam lifted Castiel up in his arms. His legs wrapping around his waist. 

“I know this is very new and probably a little strange, but just relax and you wont have to worry about ha thing.” Sam whispered.

“Thank you.” Sam guided Castiel’s head to his shoulder and cradled his head. Sam walked around the room a bit.

“Am I heavy daddy?”

“No, sweet boy. You’re as light as a feather.” Castiel smiled. Sam was good at this. “Does my baby boy want a pacifier?” he looked at Castiel who nodded. Sam picked it up and brushed it against Castiel’s lips. Castiel accepted it. He smiled around it. Sam rubbed a hand on his back. “You’re daddy’s good boy.”


	19. Daddy and his baby

Sam sat against the wall, cradling Castiel and feeding him a bottle. This was very relaxing for both men.

“Sweet boy, can daddy tell you a secret?” Castiel nodded. “I prefer the non-sexual age play. Of course, with Gabriel, it was a punishment and he wanted to do some sexual acts. I did not mind one bit, it is what he wanted. However, I much rather this.” Castiel smiled. 

Sam placed the bottle down and the pacifier back in Castiel’s mouth. He lifted Castiel up and laid him down on the bed. Sam ran a hand up and down the diaper, feeling if it was dry. He laid down beside Castiel and Castiel straddled him and rested his head on Sam’s chest. Sam rubbed a hand on Castiel’s diapered butt.

“You’re such a sweet boy, baby. You make daddy proud.” Castiel wrapped his arms around Sam’s neck and nuzzled his neck a bit. “You drank most of that bottle, so daddy expects you to use the diaper.” He soothed and Castiel blushed. Sam stroked his cheek. “You don’t need to be embarrassed.”

A few minutes later Castiel started to squirm. He rolled off Sam, embarrassed to on him. Sam rubbed his hand on Castiel’s stomach. Not pressing on it. Just rubbing, hoping to relax him. Castiel looked a little surprised when he started to pee. 

“Uh oh” he said around the pacifier.

“Uh oh.” Sam smiled and kissed is forehead and then his nose. Castiel smiled.

Sam grabbed gloves and put them on. He grabbed the changing mat. He lifted Castiel’s legs and bum and slid the mat under. 

“Okay, baby keep those legs up.”

“Otay, daddy” 

Castiel sucked on the pacifier, finding it oddly calming. Sam too the wet diaper off and grabbed some wipes, cleaning Castiel. He slid the diaper off and rolled it up. He slid a fresh one under him and grabbed some diaper cream.

“Can’t risk my sweet boy getting a little rash” Sam cooed and rubbed the cream on Castiel. He powdered him and did the fresh diaper up. He took the gloves off and blew a raspberry on Castiel’s stomach.

Castiel giggled and Sam removed the mat, lifting Castiel in his arms. He rubbed a hand on his back and swayed side to side. He bounced Castiel a bit.

“How did that feel baby? Peeing in the diaper, was that okay?” Castiel nodded.

“Yeth, daddy” he said around the pacifier.

“Good. Daddy loved changing you. You looked so small and innocent.” Castiel giggled and hid his face. “Sometimes my baby is a big boy, isn’t he?”

“Uh huh.”  
“And a pretty girl.” He cooed Castiel giggled. “That’s when my baby is not so innocent, isn’t that right sweet boy?” Castiel giggled and nuzzled into Sam’s neck a bit more. Sam kissed his forehead. “You okay?” 

“I am tho sappy” Castiel looked up beaming at Sam through the pacifier. Sam stroked his cheek. 

“I’m so glad to hear that.”

“You happy?”

“Yes, baby, daddy is so happy.” 

That night, Sam got Castiel out of the diaper and helped him shower. Castiel got dressed and Sam had in straddle his lap. Sam held him close.

“Thank you, Sam. I didn’t know I needed that, but apparently I did.” Sam stroked his hair.

“You’re welcome baby. Castiel, anytime you need that, you let me know. I enjoy our kinky adventures and the roleplaying we do, however this was perfect.

“I love you so much, Sam. You’ve taught me so much. You’re an amazing dom.” Sam rested his head on Castiel’s.

“Thank you for saying that. You have no idea how amazing it feels to be loved by a sub. Don’t get me wrong, Gabriel and I loved each other. However, you were so willing to let me into your world and I am so thankful for that.”

The boys stayed like that, in silence for a bit. Castiel started to rub against Sam. 

“Castiel?” he asked.

“Sam, please. Let me reward my dom. My daddy.” Castiel said sincerely, cupping Sam’s cheek.

“Okay, baby.” Sam kissed him and Castiel got off his lap and sank to the ground


	20. Take a break

It was almost end of the year. Castiel was studying really hard. Sam too. Sam came home one day from class and saw Castiel looking at his books and crying. Sam rushed over and wrapped his arms around Castiel.

“Baby, what’s wrong?” he whispered.

“It’s just a lot of pressure. My exam is in two days.” Castiel cried.

“It’s 1pm, take a break.”

“Daddy?” Castiel whimpered and Sam knew that tone. He smiled and kissed the top of Castiel’s head.

“Come on, sweet boy. Let daddy get you in a diaper, hm?”

Castiel nodded and stood up. Sam smiled softly and kissed his forehead, wiping his tears. He pulled off the older man’s shirt and sweatpants. He was wearing black lace panties. Castiel blushed and Sam smiled, pulling those off as well. Sam put latex gloves on and lifted Castiel, naked into his arms.

“Hold tight, baby.” Sam said and Castiel latched on.

Sam placed the changing mat down and then laid Castiel down and he automatically lifted his legs. Sam tickled his stomach.

“What good boy, helping daddy.”

Sam grabbed a diaper he kept in a drawer. He grabbed the pacifier and brushed it against Castiel’s lips. Castiel took it, sucking on it. Sam grabbed the diaper cream and put it on.

“Nnn” Castiel squirmed frowning.

“Aww, sorry baby.” Sam pouted. He powered him and did the diaper up. He took the gloves off and folded the mat. Sam reached under his bed and grabbed a blue fuzzy blanket. Castiel giggled. “Yeah, nice, soft blanket for my sweet boy.”

Sam lifted Castiel in his arms. He sat down, and wrapped him in the blanket.

“Tank ‘ou daddy” Castiel smiled.

“You’re so welcome, baby.” Sam laid down. He noticed Castiel’s eyes droop. Sam cradled his head to his shoulder. “How about a little nap, sweet boy?”

“Otay, daddy.” Castiel mumbled. 

Sam smiled down at is baby boy. Castiel sucked happily on his pacifier, Sam ran his fingers through Castiel’s hair. He was kind of happy that this is what Castiel wanted to do recently. Sam couldn’t help but laugh a little when Castiel started snoring. He only did that when he was really tired and stressed. Twenty minutes later Sam rubbed a hand down Castiel’s hand and butt.

“Sweet boy, time to get up.” Sam whispered. 

Castiel yawned and dropped his pacifier, smacking his lips. He rubbed his forehead on Sam’s shoulder. Sam picked up the pacifier and Castiel rolled off Sam and onto his back. Sam smiled rubbing his hand on Castiel’s chest.

“Did you have a good nap, baby?”

“Yes, daddy” Castiel smiled sleepily.

“You were really tired. Want to know how daddy knows it?” he cooed.

“How?” Castiel asked innocently.

“My little baby was snoring.” Sam smiled and kissing his nose. Castiel giggled and reached up stroking Sam’s hair. Castiel started peeing and he looked down. “Aww, some need a diaper change?” 

“Yes daddy” Sam place a peck on his lips and put the pacifier back in his mouth.

“Do you know how cute you are?” he cooed at Castiel as he pulled on latex gloves.

“Daddy is cute too” Castiel giggled. 

Sam lifted Castiel’s legs and once his diaper was all changed he took the gloves off and lifted Castiel in his arms with the blue blanket.

“Daddy?” Castiel asked.

“Yeah, sweet boy?”

“Can you put on a glove and stroke my cheek?” Castiel blushed and Sam kissed his forehead. 

“Of course, baby.”

Sam pulled on a glove and stroked Castiel’s cheek. He walked to the bathroom and stood in front of the mirror. He pointed in the mirror with the gloved and then stroked Castiel’s cheek.

“Look, baby. Look how cute you are.” Castiel looked in the mirror and then hid his face blushing and then looking in the mirror a bit. Sam chuckled. He bounced Castiel a bit. “You’re daddy’s good boy. Yes you are.” Castiel giggled. “You’re cute little nose” Sam booped Castiel’s nose. “Your cute lips and pacifier” He tapped Castiel’s pacifier. “You’re so perfect, baby.”


	21. A little rougher

“Sam?” Castiel asked and Sam looked up.

“Yeah, baby.”

“I would like to try something I little rougher”

“You are?”

“Yes. I-I had a scenario.” Sam smiled and nodded.

“I am an escort that you hire for the night. We both like it a little rough. I was thinking of maybe getting a motel room?”

“Sure thing baby. I really like that idea.”

“I…I would be dressed up like when we did the cop roleplay.” Sam smiled and got up and kissed him. I will get the motel room.”

That weakened Sam got two motel rooms. So Castiel could get changed. Sam was dressed in nice work pants, a button down white shirt, sleeves rolled up and blue striped tie. 

Castiel put on black lace panties, a short black dress, thigh high boots. He did the make up the same, cat eye eyeliner, bright red lipstick. He walked to the door and knocked on it. Sam opened the door.

“Hi.” Castiel said leaning against the door.

“Roxy, is it?” Sam asked raising an eyebrow. 

“Uh huh.” Castiel said running a hand down Sam’s chest. “You going to invite me in, big boy?” Sam smirked, laughing a bit. 

“Yeah, come on in.” Castiel walked in and closed the door. 

Castiel walked in the room and Sam ran a hand down Castiels back to his ass and gave it a firm squeeze and then a slap. Castiel turned around.

“Easy, cowboy. Let’s not get ahead of ourselves. It’s 200 for the night.”

“Got it covered” Sam said reaching into his pocket and pulled the money out leaving it on the dresser. 

“Good. So, you like it rough?” Castiel smirked loosening Sam’s tie. Sam gripped Castiel’s wrist, giving him a devilish grin.

“Uh huh. You will refer to me as sir.” he stepped closer, closing the space between them and leaned in to whisper in his ear. “Understood?”

“Yes, sir” Castiel breathed.

“Good girl” Sam stepped back and let go of Castiel’s wrist.

Sam kissed Castiel’s lips and started to caress his arms. Sam kissed down Castiel’s jaw and started to suck.

“Going to mark you up.” He growled “On the bed, bend over.”

Castiel bent over and the bed, Sam took his tie off and leaned over Castiel and pinned his arms to the bed, beside his head. Sam pushed the dress up and started massaged Castiel’s ass. He gripped his hips firmly. Sam rubbed himself against Castiel’s ass. He pulled the panties down and started spread Castiel’s cheeks apart.

“Mmmmm, what a nice pussy you have” Sam gave it a lick, swirling his tongue around.

“Sir, you’re paying for me, let me please you.” Castiel purred. 

Sam gave a sharp smack to his ass and stood up. He sat on the bed and Castiel stood up. Castiel straddled Sam’s lap and kissed his neck while unbuttoning a few of his buttons. One of Castiel’s hands moved to Sam’s hair and the other went and palmed his crotch. He placed open mouth kiss on Sam’s throat. Sam’s hands went to massage Castiel’s ass.

“That’s it. Just like that.” Sam said. 

“Uh huh, you like that?” 

“Show me what else you can do with that mouth of yours.”

Castiel smirked and got off of Sam and got on his knees. He undid Sam’s pants and the looked up.

“Something wrong?” Sam asked.

“Any kinks?” 

“There are latex gloves on the dresser. Why don’t you go grab them.” Sam smirked.

Castiel got up and then went to the dresser. He grabbed two pairs of gloves and the lube. When he came back Sam had his pants off. Castiel put the gloves down and lube. He slipped on the gloves. He looked up at Sam and saw him semi hard. 

“Sir, are you ready?”

“Yes”

Castiel wrapped his mouth around Sam’s cock and cupped his balls, massaging them. Sam let out a groan. Castiel smiled. Sam gripped Castiel’s neck and pushed him forward. Castiel happily sucked and rubbed Sam’s inner thighs. 

 

“That’s enough.” Castiel pulled off with a pop.  
Sam reached over and put gloves on himself. He Castiel passionately. Castiel unbuttoned the rest of Sam’s shirt and pushed it pulled it off of him. Sam gripped Castiel’s chin.

“Strip and get on your hands and knees.” He brushed his thumb over Castiel’s lips smudging the lipstick.

Castiel got out of the dress, the panties had been tossed. He kept the boots on. He got on his elbows and knees. Sam poured lube on Castiel’s ass and then rubbed a finger over it.

“I’m going to fuck you so hard, but you’re not going to cum until I say, are you?” He pushed a finger in and Castiel yelped.

“No sir.”

“No, because you’re a good girl” he cooed

“Yes, sir” Castiel purred again. 

Sam worked another finger into Castiel’s hole and then a third. Castiel gasped.

“Hm, you got a greddy little pussy, don’t you?” 

Sam pulled his fingers out and slid into Castiel. He thrusted harder and leaned forward pinning Castiel’s arms at his sides again. With his clean gloved hand He pinned Castiel’s head down and started to moved faster. Castiel panted and shut his eyes.

“Yeah? You like that?” with his other hand he spanked Castiel’s ass. 

Sam stilled his movements and leaned forward nipping at Castiel’s neck. He sucked a bit again. Not too hard, just to leave a mark. He went back to fucking Castiel. He pulled out and took the dirty glove off, leaving the other one on. He flipped Castiel over onto his back. Sam slid back into him.

“Rub your clit, but don’t you dare cum” He commanded. Makeup running down his face from the tears he reached down and rubbed his clit. Sam’s gloved hand found its way to Castiel’s throat and he didn’t squeeze, but he left it there. He leaned down and kissed him roughly. Sam pulled away. “Suck your finger.”

With his free hand, Castiel sucked his gloved finger. He moaned and moaned. Sam kept his hand on Castiel’s throat. He grunted and Castiel clenched around his cock. Castiel needed to cum and Sam knew this. 

“CUM!” he demanded and Castiel did, screaming.

Sam spilled inside of Castiel and removed his hand, he pulled out and took the glove off. He took a few deep breaths. Castiel also took the gloves off. Sam got up and handed Castiel his dress and panties. 

Sam went to the bathroom, wiped himself off and came back wearing pajama pants. When he came out, Castiel was dressed.  
“Money’s on the dress. You can go.” Sam said.

“Yes sir.” Castiel said shakily. He knew that as soon as he got into his room, Sam would be right there taking care of him. Castiel took the money . “Goodnight.”

“Uh huh” Sam said and Castiel left.

**Notes for the Chapter:**

> SO. MUCH. FLUFF AND AFTERCARE NEXT CHAPTER!


	22. Aftercare

Castiel walked into the motel room. Makeup rubbing all over his face lipstick really smudged. He placed the money down and whimpered a few times and there was a knock on the door. Castiel left it unlocked and Sam walked in with a water bottle.. Castiel looked at him with tears in his eyes. Sam wrapped him in a hug and pulled him close and kissed the top of his head.

“Baby you were fantastic.” Sam whispered.

“Th-thank you” Sam cupped Castiel’s chin and made him look at him.

“Alright, sweetheart, let’s get you in in a nice warm bath. I want you to drink this first.” 

Sam held the water bottle to Castiel’s lips and he drank a bit. Sam pulled the dress off of Castiel and the panties. He reached down and unzipped the boots. Sam led Castiel to the bathroom. He closed the toilet led, set a towel down and sat Castiel on the toilet. Sam caressed Castiel’s cheek and kissed his lips. 

“I love you” Castiel whispered

“I love you too” Sam smiled. He started the bath, got it nice and warm. He grabbed shower gel for the bubbles. 

“Can I look at my face?”

“Yeah” Castiel stood up and looked in the mirror. He smiled a bit.

“I love when you smudge my lipstick.” Sam wrapped his arms around Catiel’s waist.

“Yeah?”

“Yeah” 

Sam rubbed a thumb over one of the marks he made. He helped Castiel in the bath and grabbed the makeup remover.

“I can-“ Castiel said and Sam shook his head smiling.

“Castiel, I’m going to do all of this. Okay. You just rest.” 

“Will you give me a massage?” Castiel whispered.

“Yeah, baby. I’m going to give you a nice long massage,” he cooed. Castiel closed his eyes as Sam wiped his face. “Going to get you all comfy, going to hold you all night long. You were such a good boy for me. Such a good pretty girl.” 

When Sam was down wiping the makeup off. He grabbed a face cloth and started to gently wash Castiel’s face, neck, behind the ears. He then moved to his shoulders, squeezing a bit. 

“I liked it, Sam. I really like when we roleplay. Is there anything you’d like to try?”

“I was thinking maybe student teacher. Either as my sweet boy or pretty girl.” Sam washed Castiel’s chest.

“That would be fun.” Castiel yawned a bit.

“Need you to stay awake, baby.” Sam chuckled.

“I’m trying” Castiel smiled sleepily. 

Once Castiel was washed, Sam pulled him out and wrapped a large towel around him and dried him off. He led Castiel to the bed and had him sit down. Sam grabbed some more water and a few energy bars and some Chocolate. He got the warm duvet the brought and wrapped it around Castiel. He then got on the bed and held up the water for him.

“Here baby, drink some more. I have some food for you too.”

“Okay.” Castiel smiled and he sipped the water and took some chocolate.

“There. I’m going to hold you for a few more moments, then I’m going to get the lotion and give you a nice massage and you can sleep.” 

“Thank you, sir. Sam.”

A few minutes later Sam got up and grabbed the lotion he had Castiel lie on his stomach. He straddled his legs and squeezed some lotion on his hands and rubbed them together. Sam started on Castiel’s shoulders and up Castiel’s neck.

“Ooooo” Castiel moaned. 

“That’s it baby. Just relax. You’re so tense. “

Sam rubbed between his shoulder blades, working a knot out. Castiel closed his eyes and relaxed as Sam’s hands traveled down his back. Sam grabbed more lotion and moved down lower. Finally he asked Castiel to roll over. 

“Mmmm” he whined. Sam chuckled.

“I know, sweetheart. But I’m going to do your legs, arms and head. You just fall asleep.” 

Castiel did fall asleep and Sam tucked him into bed and crawled in with him. He held his boyfriend close, Castiel was so perfect.

**Notes for the Chapter:**

> Ideas?


	23. Chapter 23

**Notes for the Chapter:**

> Short, but I hope you like it.

Castiel had makeup on and his favorite short black flowy skirt and his favorite floral crop top. He slid his black panties on and heels. Sam had his final exam for the year. Sam had put the plug in Castiel before he left for his exam. Sam walked in and smiled at the sight.

“Welcome home sir.” he smirked.

“Mmm, sweetheart, I love it.” Sam walked over and kissed Castiel. He leaned down and nipped at his neck. “Where’s your gag?” Castiel smiled and went to get it. He handed it to Sam, Castiel walked over to the drawer with the gloves.

“What are you doing, baby girl?” Sam asked grabbing Castiel’s ass.

“Going to give you a really sexy dance sir.”

“Let me put your gag in first.”

Castiel grabbed the gloves and turned to face his boyfriend. Sam kissed him and then gripped his chin. Castiel opened his mouth and Sam smiled. He placed the gag in and secured it. 

“Okay, baby. You want to give me a sexy dance, go ahead.” 

Castiel swung his hips side to side and pulled on the gloves. Sam groaned and undid his pants, pulling his cock out. Castiel slowly put one glove on and snapped it. He did the same with the other one. With one hand he rubbed the back of it on his face. The other he ran down his front of his skirt. 

Castiel kept swinging his hips and turned around. He looked over his shoulder and spanked his own ass. Be bent down, pushing his ass out and rolling back up. He heard Sam putting on a glove. Castiel turned around and ran his down his neck and the other across his stomach. 

Sam’s eyes were on him the hold time. Meanwhile he was pumping his cock. Castiel bent down and spread his legs flashing Sam his panties. He stood back up and walked over to Sam. He straddled him and ran a finger across Sam’s lips and Sam started to suck Castiel’s finger.

Castiel’s other hand went to Sam’s cock. Sam’s hands went and squeezed Castiel’s ass. Castiel rolled his hips. The two boys never broke eye contact. The look in sam’s eyes made Castiel hard. His boyfriend all dolled up, with the gag was perfect. 

Castiel took his finger out and held on to Sam’s shoulder for balance. Sam took the opportunity to place open mouthed kisses along Castiel’s neck. Sam’s grunts, Castiel knew he was getting close.

Castiel got off of Sam and knelt in front of him. Sam was a little confused be this, but when Castiel was on all fours sitting back face inches from Sam’s cock. Sam wrapped his hand around his cock. Castiel nodded. A few more pumps and Sam came on Castiel’s face. Castiel waited for Sam’s breathing to even out a bit. Sam cupped Castiel’s cheek with his gloved hand.

“Look at my perfect girl. Wanting to please me so badly. Giving me a beautiful dance and letting me give her a facial. You’re a beautiful sight, baby doll. Mind if I keep you like this? I need to start packing up, I would love to look at you like this while I do.” Castiel tried to smiled and nodded. “Good girl. Here’s how I want you. up on the desk, back against the wall, legs spread wide. Gloved hands on your thighs, head looking forward.” Castiel did as Sam told him. Sam took the glove off and threw it away. He looked back at Castiel “Very good.”

**Notes for the Chapter:**

> *Cries and throwself on the ground* can someone pleeeeaaase fanart that image of Castiel, agaisnt the wall, legs spread, panites showing, gag in mouth, gloves on.


	24. Chapter 24

**Notes for the Chapter:**

> Not the best, but it's setting it up.

Sam and Castiel hadnèt seen each other for two weeks since they got on break. Gabriel and Dean were going up to the cottage though and they told Sam to invite Castiel. The two boys were excited to see each other. Castiel jumped in Sam’s arms and the two started to make out.

“I missed you, baby. I missed you so much” Sam said.

“I missed you too” Castiel said. Dean and Gabriel came out of the cottage, laughing a bit.

“There is a beautiful sight.” Dean smiled.

“Welcome” Gabriel said. Sam put Castiel down.

“Dean, Gabriel, it’s nice to see you again.” Castiel smiled

Once Castiel and Sam got settled in their room they went downstairs. Dean handed them a beer and they all sat down. Castiel on Sam’s lap.

“We have a play room here, so Gabe and I may sneak away from time to time.” Dean said. 

“You two are free to use it.” Gabriel smiled and Castiel blushed.

“This is going to be an open weekend. Castiel, anytime you want to go get dolled up, you do.” Dean smiled.

“What about…”Castiel looked at Sam. They have been very open with the other two.

“If you want to be a baby and have daddy take care of you?” Sam whispered. Castiel nodded.

“Cas, Dean and I do pretty much anything and everything. We will tone it down a bit this weekend, so we don’t make you uncomfortable. But if you need to regress for a bit, go ahead. We’re here to take care of you.” Gabriel reassured him. 

“You guys don’t need to hold anything back from us.” Sam spoke up. The two nodded

“In that case, Sammy would you be okay with me being naked?” Dean asked.

“Dean, we grew up together. It’s fine.”

“Good, Gabriel and I will be naked.”

“I would like to get all dolled up.” Castiel said.

“Let’s all get ready” Dean said

While Sam and Castiel got ready, so did Dean and Gabriel. Dean kissed Gabriel

“You will be wearing your cock cage” Gabriel was sitting on the bed and Dean knelt in front of him and placed the cage on hm. 

“Sir?” Gabriel asked.

“Sweetheart, you can call me Dean all weekend.” Gabriel smiled. Once the cage was on. Gabriel stood up. “Bend over” Dean growled. Gabriel smirked. 

Sam and Castiel were snuggling and they heard moans coming from the other room. Castiel smiled a bit.

“Baby girl, your plug is in; you’ve got a pretty floral dress on.”

“Thank you, sir.”

Dean spilled into Gabriel, pulled out and plugged him up. Dean lifted Gabriel up and held him close. 

When Castiel and Sam went downstairs they saw Gabriel warming Dean’s cock. 

“Aww, you look beautiful.” Dean cooed at Castiel.

“Thank you, Dean.” 

Dean gripped Gabriel’s hair and Gabriel moaned a bit. He started to move his head. Sam slipped on a latex glove. Castiel sat on his lap and Sam reached up and Castiel started to suck on two of Sam’s finger. Dean pulled Gabriel’s hair and Gabriel let go with a pop.

“Came in my boy and plugged him up.” Dean cooed. “is that right?”

“Yeah” Gabriel smiled.

“Nice.” Sam smiled. 

“Your girl seems to like that” Dean chuckled. 

“Yeah, she really does.”

“Going to take Gabriel to the play room for a bit.” Dean attached a leash to Gabriel and led him to the play room.


	25. Chapter 25

While Dean and Gabriel played Sam took Castiel upstairs. Sam took the glove off and kissed Castiel passionately, grabbing his ass and kissing down his neck. 

Meanwhile in the playroom, Dean had Gabriel restrained to the table, ass up. Dean snapped on latex gloves. The cock cage was still on. He eased the plug out and grabbed the silicon anal beads. He poured some lube on Gabriel’s hole and rubbed it.

“Sir!” Gabriel gasped. Dean lubed up the anal beads. 

“Relax.” Dean soothed. 

Dean pushed one anal bead in Gabriel’s ass. Then he pushed another one in and then pulled it out. Dean pushed the second bead in and then lubed up the third bead and pushed that in. Gabriel whined each time one went in. 

“There’s a good boy.” Dean praised. 

Once all the beads were in, Dean pulled two out. Gabriel wanted to cum, but he wasn’t allowed to. Dean pushed the two back. He pulled the gloves off and then unstrapped Gabriel. He grabbed a vibrator and then attached his leash and led him back to the living room.

Castiel had decided that he wanted to go in his little space. Once Sam got him diapered he grabbed the pacifier and placed it in Castiel’s mouth. He grabbed the fuzzy blanket and carried Castiel down the stairs. 

“Aww, look at that baby, Dean and Gabriel are done.” Sam cooed. Castiel giggled and hid his face.

“Hey, baby boy” Dean cooed and Castiel waved.

“Toy” Castiel said pointing to the anal beads in Gabriel’s ass. Sam bounced Castiel a bit, Dean had the cock cage off.

“Yeah, baby, toy.” Sam kissed his cheek.

“Do you want to play with the toy?” Dean smirked and Castiel nodded.

Sam knelt down and spread out the fuzzy blanket. He placed Casitel down. Sam knelt behind Castiel and rubbed his back. Dean slipped on latex gloves and grabbed the lube.

“See the loop? Pull on that, sweetheart.” Dean instructed.

Castiel pulled the loop and one bead popped out. Castiel giggled and Gabriel smiled up at Dean. He pulled it again and another bead popped out. 

“You know what’s good idea? If you pull it really slowly.” Dean said.

Castiel happily sucked on his pacifier. Sam leaned forward and kissed the side of his head. Castiel pulled really slowly, Gabriel moaned. Dean turned the vibrator on low. He held Gabriel’s cock and ran the vibrator up and down his shaft.

“Ooooooooh” Gabriel moaned. 

“Good job baby.” Sam praised Castiel. 

“That’s a good job.” Dean smiled at Castiel.

Castiel pulled the beads out completely. Dean stopped the vibrator and took the beads from Castiel. Sam pulled Castiel against him and held him close. Dean got behind Gabriel and lubed up the beads and started to push them back in. Sam lifted Castiel up in his arms.

“Daddy’s going to get his baby a nice bottle, how does that sound?” Sam smiled rubbing his nose against Castiel. 

“Aww, Cassy, you and your daddy are so cute” Dean smiled.

“Tank ou.”

Dean kept teasing Gabriel while Sam fed Castiel.


	26. Chapter 26

“Aww, sweet boy, let daddy change your wet diaper” Sam cooed at Castiel. He handed Castiel to Dean, who had Gabriel sobbing and begging to cum. 

“You’re a good boy for your daddy, aren’t you?” Dean cooed.

Sam placed the changing mat down and slipped on latex gloves. He took Castiel from Dean and undid his diaper. Castiel lifted his legs up, while Sam grabbed the wipes.

“Please!” Gabriel begged.

“Ooh, daddy. It cold” Castiel shivered a bit. 

“Aww, daddy is sorry baby.” Sam pouted. 

Dean snapped on latex gloves. He grabbed the lube and Gabriel whimpered. Sam placed a new diaper under Castiel and powdered him and did it up. He leaned down and blew a raspberry on Castiel’s stomach. 

“There we go” Dean praised Gabriel as he slid two fingers in his ass. 

“Sir!” Gabriel sobbed when Dean wrapped his hand around his cock. Sam lifted Castiel up in his arms.

“My baby boy is going to have a nap” Sam bounced Castiel.

“I’ll make sure my boy keeps quiet.” Dean said

Sam carried Castiel up to the bedroom and laid him down. He covered him up with the blanket rubbed a hand on his back while Castiel sucked on his pacifier. 

“Daddy, hold” Castiel mumbled.

“Okay, baby boy.” Sam smiled

Sam wrapped his arms around Castiel and held him tight. 

Gabriel was crying, Dean’s hands were still in him and on him, but he stilled them. Dean loved teasing his sub. Dean removed his hands from his sub. Gabriel placed his head on the floor, lowering his head.

“Aww, look at you. So needy.”

“Please, sir! Daddy. Plea-heas-hease.” He sobbed

“Shhh. Little Cassie is sleeping. Be a good sub and stay quiet.” 

Half an hour later Castiel woke up. He smiled and rolled over to kiss Sam.

“Mmm, boy big?” Sam mumbled.

“Yes, sir. I want to be your good boy.”

“Okay, you will be. Is your diaper wet?”

“Yes.”

Sam reached over and snapped on some gloves. He got Castiel out of the diaper and wiped him. He pulled the gloves off and looked at Castiel.

“Sweet boy, I’m wondering if you would like to stay naked for the rest of the day. If not, that is very okay.”

“I’ll be naked, I am excited about that.” 

“Good. So will I. Now, I did not hear a scream from Gabriel, so I am assuming that Dean has not let him cum.”

The two men walked downs stairs to find Gabriel and Dean in the playroom. 

“Boys, come on in, if you’d like.” Dean called out.

Sam held Castiel’s hand and led him to the playroom. Castiel gasped when he saw it. There was a medical chair, whipping bench. Chains, padded table. Various toys and tools around the wall. 

“Oh, look at that. You’re both naked, very nice.” Dean smiled.

Gabriel was chained up. Vibrator was in his ass. Dean pushed the button and Gabriel screamed and screamed. Dean gave him a few strokes and finally Gabriel came screaming. Sam had his arms wrapped around his sub and stroked his hair. 

“Very good.” Dean praised and he turned the vibrator off and pulled it out. He unchained Gabriel and lifted him in his arms. “Good boy. You’re a good boy. Let me get you all cleaned up.” He whispered and walked out of the play room.

“Sir” Castiel said.

“Sweet boy, we’re showing you this room because, the three of us would like to help you with a fear that you have”

“You are?”

“Yes. We would like to help you with your fear of doctors.” Sam kissed Castiel. 

“Oh…uh…”

“You are nervous, we will be very gentle with you. I have spoken to Dean and Gabriel, they would love to help”


	27. Part 1-medical exam

Sam, Dean and Gabriel sat down with Castiel the next morning to talk about what they would be doing. 

“Castiel, it will be roleplaying today” Sam said. “Dean and I will be doing the procedure; Gabriel will be there to keep you calm.” Castiel nodded. Gabriel reached over and grabbed his hand.

“We will be giving you two shots.” Dean stated.

“Wha-what?” Castiel gulped.

“Baby, it will be alright. We are all here for you. You got sick in college”

“You took care of me” Castiel said

“Yes I did. However, you really needed a doctor.”

Once everything was settled Dean and Sam got dressed and ready. Castiel and Gabriel also got dressed. Gabriel led Castiel to the play room. He held his hand and rubbed a hand on his back.

“Everything is going to be okay.” he said.

“I know. I’m a little more excited. I know that they’ll take good care of me.”

“We talked a lot about who would be taking you to the appointment. Sam wanted to be the one who is doing the exam. I hope you’re comfortable with me, being the one who’s calming you.”

“I am Gabriel.” 

Gabriel knocked on the door and Dean opened it. He was in nice dress pants and a button downed shirt and a stethoscope around his neck. 

“Castiel, come in” Dean spoke.

Gabriel and Castiel walked in. Sam was also in the room, dressed similarly to Dean, except he has a white lab coat. 

“Good morning, Castiel. My name is Dr. Winchester and this is my partner and brother, nurse Winchester.”

“Hello, sir.” 

“Castiel, I’d like you to undress completely” Sam spoke.

“Unfortunately, we are out of gowns.” Dean added.

Castiel got undressed, blushing a bit. He folded his clothes and placed them on the chair. Sam smiled and Dean patted the medical table.

“Castiel, please sit on the table. I will have Nurse Winchester take your vitals, I’m going to prepare the needle.” Castiel swallowed. “It’s alright, Castiel, we’re going to take it slow.” 

Castiel sat on the table and Dean took his right wrist and looked at his watch.

“Nice slow breaths for me, Castiel.” Dean spoke.

Gabriel stepped forward and rubbed a hand on Castiel’s back. Dean nodded. He went and grabbed a blood pressure cuff and wrapped it around Castiel’s left arm. Dean took the stethoscope bits in his ears and placed it on the inner elbow. Gabriel rubbed a hand on Castiel’s neck. 

“Very good.” Dean said taking the cough off. 

He listened to Castiel’s heart and lungs and took the stethoscope off. He walked over and grabbed latex gloves. They all hear Castiel audibly gasp.

“Castiel” Sam spoke calmly. “Nurse Winchester is just going to take your temperature rectally. That is all.” Sam nodded. “Please turn on your elbows and knees.” 

Castiel still looked worried. Sam walked over and placed a hand on his cheek, stroking it.

“I’m-I’m sorry, Dr. Winchester.” Castiel whimpered. 

“Shhh. No need to be sorry. What I need you to do is get on your elbows and knees. Can you do that for me?” Castiel nodded.

Sam took a step back and Castiel got off the table and back on how Sam asked. Gabriel was by Castiel’s head and stroked his hair. He shuddered when he felt a latex glove on his lower back.

“It’s Nurse Winchester. I’m going to take your temperature, now, that it all.” 

“Yes sir” 

The familiar popping of the cap echoed the room and Castiel felt a lubed glove finger rub his hole. Castiel relaxed and Dean pushed his finger in. He moved it around and pulled out. Dena lubed the thermometer and slid it in. 

“You’re doing a good job, Castiel” Sam praised.

Dean pulled the thermometer out and he pulled the latex gloves off. Sam slipped on latex gloves and Dean’s warm hands touched Castiel’s butt and back.

“Alright, we want you to stay just like this.Just like this and it will all ber over soon.” Dean said.

Castiel looked back seeing Sam tap the needle.


	28. Chapter 28

**Notes for the Chapter:**

> I'm sorry. My heart just isn't in this story any more.
> 
> Here is a very short ending.

“I’ve got you baby, I’m here.” Sam soothed Castiel. He had been such a good boy during the medical exam. The needle was a bit of a struggle. Gabriel and Dean had to restrain him. 

Sam continued with the exam noticing instantly when Castiel’s breathing picked up. Dean and Gabriel exited the room and left the alone. Once Sam had him calm, he took Castiel upstairs and placed him on their bed, wrapping him in a blanket. He stroked his hair.

“Baby, what can I do?” Sam whispered.

“I failed you.” he whimpered.

“No you didn’t. Oh Castiel, you were so brave today.” Sam crouched down so he could be level with Castiel’s face. “You were such a good boy.” 

“Ca-Can you hold me?”

“Yeah baby” Sam climbed on the bed behind Castiel and wrapped his arms around him. “I love you so much, sweet boy. You are a beautiful sub for me. A beautiful boyfriend. Dean and Gabriel are so proud of you.”

“They are?” Castiel whimpered.

“Yeah.” 

A little while later Castiel and Sam went downstairs. Gabriel had made them soup, while Dean made tea.

“How are you feeling?” Dean asked going over and hugging Castiel.

“Much better, Dean. Thank you.” Castiel whispered.

Sam and Castiel didn’t do much the rest of the weekend. Sam just needed to make sure that his boyfriend was okay. Felt safe. With his old Dom, Sam just needed him to know that he was there. That he was safe

**Notes for the Chapter:**

> I'm working on a very kinky medical fetish story. That I will have up in a few days. 
> 
> Thank you for following along and sorry fro this chapter and ending

**Author's Note:**

> comment. Kudos


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